boston area trips

Boston Itinerary: How to Spend Five Days in Boston

One of the most historic cities in the United States , Boston is the city I called home for the first 25 years of my life.

More a collection of towns than a metropolis like New York , Boston is a city steeped in history (it contains a lot of historical firsts for the United States and played a pivotal role in its founding), delicious food, wide-open green spaces, first-rate museums, and warm, welcoming people.

Visiting Boston offers all the benefits of a big metropolis without the intensity and fast pace of New York.

Boston is easy to get around and compact, making it perfect for travelers. The subway will take you wherever you need to go.

So how many days do you need to visit Boston?

Most people visit for three to four days, and I think that’s a perfect amount of time. As someone who’s lived there, I can say that, since Boston is so small, you won’t waste a lot of time “in transit,” so you can pack a lot into your days. Obviously, you can spend longer here (slow travel is the best travel), but for the first-time visitor, three to four days is enough.

Here’s a suggested Boston itinerary that will allow you to see the best of Boston:

Table of Contents

Boston Itinerary: Day 1

Boston itinerary: day 2, boston itinerary: day 3, boston itinerary: day 4, boston itinerary: day 5, other things to see and do in boston.

• Boston Common
• Massachusetts State House
• Park Street Church
• Granary Burying Ground
• King’s Chapel Burying Ground
• Benjamin Franklin statue and the former site of Boston Latin School
• Old Corner Bookstore
• Old South Meeting House
• Old State House
• Site of the Boston Massacre
• Faneuil Hall
• Paul Revere House
• Old North Church
• Copp’s Hill Burying Ground
• USS Constitution
• Bunker Hill Monument

You follow a brick road through the city, and there are signs and historical markers all along the way. Given all the walking that’s involved, I would make this the main activity of the day. You’ll want to take your time and see all the sites thoroughly.

You can also take a guided tour from the visitor’s center. Tours run hourly between 11am and 1pm, with additional tours in the afternoon in the spring and summer. Tickets are $17 USD for adults, $15 USD for students and seniors, and $8 USD for children 6-12 (free for kids under 6).

4 S Market St, +1 617-523-1300, faneuilhallmarketplace.com. Open Monday-Saturday 10am-9pm and Sunday 12pm-6pm.  

Browse for Books Located a stone’s throw away from the Boston Common, Brattle Book Shop is a family-run used bookstore that dates back to 1825. It’s actually one of the oldest surviving bookstores in the country! It’s home to over 250,000 books, maps, postcards, and other odds and ends. In addition to used books, the store is also home to an impressive collection of first editions and antique books.

9 West Street, +1 617-542-0210, brattlebookshop.com. Open Monday-Saturday 9am-5:30pm.

Walk Around the Back Bay This area used to be an actual bay. Before the Europeans arrived, the indigenous population used the tidal bay to catch fish, as the bay drained completely during low tide. When the land was colonized, a dam was built and the tidal bay was eventually filled in, creating the Back Bay area.

The end of the Public Gardens meets Boston’s Back Bay, our version of New York’s SoHo and West Village. This is where Boston’s elite and wealthy live, and nearby Newbury Street is our Madison Avenue, with lots of expensive shopping and high-end eateries. It’s a beautiful space to stroll around, with pretty brownstones and tree-lined streets. You can still see plenty of old Victorian homes in this neighborhood that date back to the 19th century. ( Here’s a list of other neighborhoods worth checking out as well!

You’ll also find the Boston Public Library here. Opened in 1852, it’s one of the largest municipal libraries in the country, home to over 23 million items, with almost 4 million visitors each year.

206 Clarendon St, +1 617-536-0944, trinitychurchboston.org. The church is open for prayer and tours Tuesday-Saturday 10am-5pm and Sundays 12:15pm-4:30pm. Tours are $10 USD for adults, though it is free to enter for worship.

Head up to the Prudential Tower Head back toward Copley to see the Prudential Tower, colloquially known as “The Pru.” You can actually go up to the top and get a bird’s-eye view of Boston. There are 52 floors in the building, which was built in the 1960s. These days, it’s the second tallest building in the city (the John Hancock Tower is first).

800 Boylston St, +1 617-859-0648, prudentialcenter.com. Open daily from 10am-8pm (10pm in the summer). Admission is $34.99 USD for adults, with discount available for students, seniors, and children.

47 David G. Mugar Way, +1 617-626-1250, hatchshell.com. See the website for an up-to-date list of events.

1 Science Park, +1 617-723-2500, mos.org. Open Saturday-Thursday 9am-5pm and Fridays 9am-9pm. Admission is $29 USD for adults, with discounts available for seniors and children.  

1 Central Wharf, +1 617-973-5200, neaq.org. Open Monday-Friday 9am-5pm, weekends 9am-6pm. Admission is $34 USD for adults, with discounts available for kids and seniors.

See the Skinny House When you’re in the North End, visit 44 Hull Street. Known as “the Skinny House” (or the Spite House), this incredibly narrow house has a rather interesting history. Built after the Civil War, it was a passion project of Joseph Euestus, who came home from the war to find that his brother had taken over more than half of the inherited land they were meant to share. Joseph decided to build on the remaining land — which his brother thought was too small to build anything on. Joseph went ahead and built a narrow four-story home on the small slice of land to block his brother’s view.

Visit an Art Gallery or Museum Boston has a lot of great galleries and museums, so depending on your interest, you’ll want to check out some (or all) of the galleries and museums below. It will take more than an afternoon to see them all but you can always spread these visits out over a few days!

• Institute of Contemporary Art : If contemporary art is your cup of tea, this is for you. While it’s not my favorite style of art, I have to admit this place does put on some insightful exhibits. 25 Harbor Shore Drive, +1 617-478-3100, icaboston.org.
• Commonwealth Museum : This museum explores the history of Massachusetts. It’s actually really interesting and entirely underrated (especially if you’re a history nerd like me). 220 Morrissey Blvd, +1 617-727-2816, sec.state.ma.us/arc.
• Harvard Museum of Natural History : This natural history museum has exhibitions showcasing dinosaurs, animals, and minerals (including meteorites). It’s a great choice if you’re traveling with kids, though there is plenty of informative content for adults too! 26 Oxford St +1 617-495-3045, hmnh.harvard.edu.
• Harvard University Art Museums : Harvard actually has three art museums – the Fogg Museum, the Busch-Reisinger Museum, and the Arthur M. Sackler Museum. They are home to both modern and historical art exhibitions. See what exhibitions are running by checking their website. harvardartmuseums.org
• Museum of Fine Arts : This museum has an impressive collection of over 450,000 pieces of fine art. It also runs all sorts of art classes throughout the year, both multi-week classes as well as single-day workshops. If you’re looking to learn something new or improve your skills, check out the website for more details. 465 Huntington Avenue, +1 617-267-9300, mfa.org.
• Warren Anatomical Museum : Founded in 1847, this macabre museum is filled with Civil War–era medical tools as well as some unique (and perhaps unsettling) medical mysteries. It’s super weird but super neat. A definite must if you’re looking for an off-the-beaten-path museum! 10 Shattuck St, +1 617-432-6196, countway.harvard.edu/center-history-medicine/warren-anatomical-museum.
• Boston Tea Party and Ships Museum : This interactive museum is home to some historic ships that have been authentically restored to show you what life was like at sea during the Boston Tea Party. It also has a really informative documentary about the events that led up to the Tea Party and the American Revolution. Best of all, you can actually throw fake crates of tea into the river yourself to see what it was like! 306 Congress St, +1 617-338-1773, bostonteapartyship.com.
• Paul Revere House : Built in 1680, this is actually the oldest building in the entire city (it’s been renovated but it’s still the original building). The museum is filled with the family’s furniture and artifacts, giving you a sense of what life was like in Boston before the Revolution. 19 N Square, +1 617-523-2338, paulreverehouse.org.
• Museum of Bad Art : The name says it all! This is a museum filled with terrible art. The MOBA has rotating exhibits throughout the year, so there is always something new and terrible to behold. If you feel like a laugh, definitely check out this quirky gallery! 55 Davis Square, +1 781-444-6757, museumofbadart.org.
• Isabella Stewart Gardner Museum This museum is home to an amazing art collection of over 20,000 items, including European, Asian, and American art. Opened in 1903, the museum is made up of a wide-ranging collection of paintings, tapestries, decorative arts, and sculptures. It’s one of the best museums in Boston. Don’t miss it. 25 Evans Way, +1 617-566-1401, gardnermuseum.org.

Harvard University, +1 617-495-1000, harvard.edu/on-campus/visit-harvard/tours.

125 Arborway, +1 617-524-1718, arboretum.harvard.edu. Open daily 7am-7pm. Admission is free.

Take the Sam Adams Brewery Tour After four days of sightseeing, you deserve a beer or five. Luckily, this brewery is located near the Arboretum so it’s easy to visit and a great way to end your day. Sam Adams is a major brewer in Boston, and locals drink it widely and frequently. The brewery offers free tours, starting in mid-afternoon and departing every 45 minutes. You get a few free samples along the way. If you’re under 21, don’t worry. You can still go — you just can’t drink.

30 Germania St, +1 617-368-5080, samueladams.com. Tours are available Monday-Thursday and Saturdays 10am-3pm. On Friday, tours are available between 10am and 5:30pm. Their Sam Signature Experience is 45 min long and costs $10 USD.

4 Yawkey Way, +1 877-733-7699, mlb.com/redsox/ballpark. See the website for an up-to-date schedule.

(The Sox not in season? No worries. We have the Bruins, Celtics, and Patriots. No matter the time of year, you’ll be able to find a game to see!)  

Visit the Children’s Museum If you’re traveling with kids, this is a great place to spend part of your visit. It’s the second oldest children’s museum in the US and has permanent exhibits on health and exercise, construction, space, art, and diversity. It also has a real two-story house from Kyoto, Japan, that teaches kids about life there (it’s actually pretty cool!).

308 Congress Street, +1 617-426-6500, bostonchildrensmuseum.org. Open Wednesday-Sunday 9am-12pm and 1:30pm-4:30pm. On the first Saturday of the month, the museum opens at 10am. Admission is $20 USD for both adults and kids (free for infants under 12 months).

Charlestown Navy Yard, +1 617-426-1812, ussconstitutionmuseum.org. The ship is open Tuesday-Sunday 10am-6pm (with extended hours in the summer); the museum is open 10am-6pm (with extended hours in the summer as well). Admission is free, though the museum has a suggested donation of $10-15 USD.

Visit More Museums – With any extra time, visit more museums! There’s plenty of them to see! Try not to skip the big ones!

725 Commonwealth Avenue, +1 617-353-2630, bu.edu/astronomy/community/open-night-observatory/. Viewings are Wednesday evenings at 7:30pm in the autumn and winter and 8:30pm in the spring and summer. Make sure to get there 10 minutes early as they don’t permit entry once it starts.

See the Mapparium – Located in the Mary Baker Eddy Library, this three-story inverted globe serves as a giant map of the world that you can walk into via a glass bridge. It is constructed of over 600 stained-glass panels and shows the world as it looked in 1935.

200 Massachusetts Avenue, +1 617-450-7000, marybakereddylibrary.org. Open daily 10am-5pm. Admission to the Mapparium is $6 USD for adults, with discounts available for students, children, and seniors.

Head to Castle Island – Castle Island is located in South Boston and is famous for Fort Independence. When the fort was no longer needed for defense, it was actually used as the first state prison. The island covers 22 acres and has excellent beaches, as well as some running trails that are popular with the locals. There’s also an area for picnics and you can visit the old fort for free. The place gets pretty busy on the weekends during the summer, and you can often see school groups exploring the fort during the spring.

Relax at the Lawn on D – This massive green space is new to the city (when I was growing up, there was nothing in this area so you would never go there). There are all sorts of free activities happening year-round, from concerts to festivities and everything in between! There’s public seating, free Wi-Fi, art exhibitions, and a few games, like table tennis and bocce. To see what events are happening during your visit, check the website for details.

420 D St, +1 877-393-3393, signatureboston.com/lawn-on-d. Open Monday-Wednesday & Friday-Saturday from 7am-11pm and Thursday & Sunday from 7am-10:30pm (hours may vary for events). Admission is free.

Hike the Blue Hills – This park is a bit out of the way, but it’s definitely worth a visit if you want to get out and stretch your legs. The 7,000-acre park is home to over 100 miles of trails and offers some picturesque viewpoints. There are also plenty of activities to keep you entertained, such as boating, fishing, skiing, and rock climbing (depending on the season). It can get busy in the summer on the weekends, so just be sure to arrive early.

Tour the Custom House – Built in the 17th century, the Custom House is one of the most recognizable buildings in the city. In 1915, a tower was added to the building, making it the tallest building in the city at the time. The building is owned by Marriott Hotels now, though you can still take a free tour (by appointment) to go up to the observation deck on the 26th floor.

3 McKinley Square, +1 617-310-6300, marriott.com/hotels/travel/bosch-marriott-vacation-club-pulse-at-custom-house-boston. Tours are free though they are by appointment only.

Boston is a great city (and I’m not just saying that because I grew up there). I’ve never encountered a person who hasn’t liked it. This Boston itinerary will give you a good overview of the city at a relaxing pace. You’ll be moving around a lot, though, so make sure you get an unlimited “T” pass (subway/train pass). If you have more time, you can squeeze in some other activities .

But why rush such a beautiful place?

Take it slow. Mix and match the itinerary to suit your needs but this is how I’d structure my days if I was visiting Boston!

Book Your Trip to Boston: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.

For the best hostels, check out this post on the best hostels in the city.

If you want to know the best neighborhoods, here’s my guide to all the best areas in town !

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (best for everyone)
• Insure My Trip (for those over 70)
• Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.

Want More Information on Boston? Be sure to visit our robust destination guide on Boston for even more planning tips!

Got a comment on this article? Join the conversation on Facebook , Instagram , or Twitter and share your thoughts!

Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

Related Posts

GET YOUR  FREE TRAVEL STARTER KIT

Enter your email and get planning cheatsheets including a step by step checklist, packing list, tips cheat sheet, and more so you can plan like a pro!

🙌 Awesome, you're subscribed!

Thanks for subscribing! Look out for your first newsletter in your inbox soon!

Get us in your inbox

Sign up to our newsletter for the latest and greatest from your city and beyond

By entering your email address you agree to our Terms of Use and Privacy Policy and consent to receive emails from Time Out about news, events, offers and partner promotions.

Awesome, you're subscribed!

The best of Boston for free.

Sign up for our email to enjoy Boston without spending a thing (as well as some options when you’re feeling flush).

Déjà vu! We already have this email. Try another?

Love the mag?

Our newsletter hand-delivers the best bits to your inbox. Sign up to unlock our digital magazines and also receive the latest news, events, offers and partner promotions.

• Things to Do
• Food & Drink
• Time Out Market
• Coca-Cola Foodmarks
• Los Angeles

The 16 best day trips from Boston

Take a break from city life and visit these nearby New England destinations—no packing required

While many of us could easily spend every waking moment in Boston, it can be refreshing to escape the city for 24 hours or so. Fortunately, this picturesque New England region offers an array of potential day trips from Boston, including quaint seaside villages, historic towns and stunning mountain vistas. So grab your pals or significant other, and hop on a ferry, train or automobile to one of these lovely destinations. Once you're back in town, you'll once again feel ready to take advantage of the  best Boston attractions ,  best free things to do in Boston  and  best museums in Boston . And when you need a little longer time away check out our list of the best weekend getaways in New England . RECOMMENDED: The Best Hotels in Boston

Been there, done that? Think again, my friend.

Best day trips from Boston

1.  newport, ri.

The Newport mansions of the Gilded Age still impress with their grandeur—just as they were built to do. If you have time to only tour one estate, check out The Breakers . Near the International Tennis Hall of Fame , the Audrain Auto Museum houses a seasonally rotating display of incredible cars inside a gorgeous Art Deco building.

Take the Cliff Walk, which has stunning views of the ocean, or relax at the public Easton’s Beach . Stroll past cool shops and eateries on narrow Thames Street. On Marlborough Street, dine at the White Horse Tavern , which claims to be America’s oldest restaurant, or duck over to The Reef at Howard Wharf for dinner and drinks with a view. Near the harbor, Bowen’s Wharf’s buildings date back to the 1700s, now offering an inviting maze of restaurants and shops. Stroll over the causeway to Goat Island where the Newport Harbor Lighthouse is overlooked by the upscale Gurney’s Resort.

2.  Portland, ME

​​Maine's largest city, located about a two-hour drive north of Boston, attracts epicureans from around the country to its cobblestone streets. Wander the charming, hilly Old Port district, where every kind of boutique imaginable touts colorful wares. Pop into one of the many quaint pubs and dimly lit cocktail bars, like the excellent Jewel Box or Blyth & Burrows —the latter of which pairs the best in innovative mixology with equally scrumptious small plates. In the West End arts district, enjoy the I.M. Pei-designed Portland Museum of Art and the State Theatre , which hosts national acts, both musical, comedic and theatrical.

The food scene here lives up to the hype:   Cong Tu Bot for nationally celebrated Vietnamese fare;  Green Elephant for an inventive vegetarian meal;   Evo Kitchen + Bar for progressive twists on Mediterranean cooking; or  Union , a vibrant locavore haunt located at  The Press Hotel , whose historic building was formerly the home of the Portland Press Herald.

3.  Newburyport, MA

The Newburyport Historic District, which encompasses most of the downtown, is listed in the National Register of Historic Places. This treasure trove of well-preserved, Federal-period architecture includes the notable Cushing House Museum & Garden , home of statesman Caleb Cushing, and the Custom House Maritime Museum , which also unravels local history. The beautiful Waterfront Park and boardwalk has regular concerts during warmer months.

Catch a play or see a show at the Firehouse Center for the Arts , grab a gourmet sandwich and bottle of wine at Joppa Fine Foods ,  relax with excellent cocktails and modern Middle Eastern bites at Bar25 ,  dine on classic seafood at The Black Cow  or head to the Newburyport Brewing Company ,  offering a friendly tap room and beer garden.

Newburyport includes part of neighboring, sedate Plum Island , a barrier island overlooking salt marshes.

4.  Gloucester, MA

Shipbuilders and fishermen put Gloucester on the map, and both industries still exist there today —just  on a smaller scale. The Fishermen’s Memorial on Gloucester Harbor honors all those lost at sea, including the Andrea Gale and its crew, the real-life victims of The Perfect Storm . Check out the Cape Ann Museum , which has an amazing collection of art and artifacts specific to Gloucester and its surroundings.

Across narrow Main Street, you can savor straight-off-the boat seafood at the chic basement restaurant  Tonno . Oak to Ember  will impress with its menu of hearty, wood-fire-cooked dishes and thoughtful cocktails. Or, if you're more about ocean views, head to the Beauport Hotel , whose 1606 Restaurant has a great deck overlooking the water. Next door to the hotel, Beauport Cruise Lines offers seasonal jaunts around the harbor.

5.  Salem, MA

Salem is forever linked to its horrifying and fascinating 1692 Witch Trials. The curious flock to the home of presiding Judge Corwin, which today is a museum known as The Witch House . Halloween is a big thing here—so are new age and cult shops. On a less spooky note, the Peabody Essex Museum houses a wonderful art collection, and Salem is the birthplace of Nathaniel Hawthorne, author of The House of the Seven Gables. You can even tour the house he may have been writing about, the 350-year-old Turner-Ingersoll Mansion.

Though it only dates back to 1930, Pioneer Village —a 10-minute drive from downtown, in Forest River Park—reenacts early 17th-century colonial life. Eat like a local at Ledger or Settler , or nerd out with old school arcade games and pinball machines at Bit Bar . 

6.  Provincetown, MA

Creative, sassy P-Town—located only a 90-minute ferry ride from Boston—is an artsy LGBT hotspot. It’s got a great mix of galleries, restaurants and nightlife hangouts. Lined with dozens of colorful shops, friendly eateries and local businesses, Commercial Street is the bustling heart of the town. Seek out one of the many events and festivals that fuel the thriving arts scene.

The famous and seasonal  Lobster Pot is the biggest name in town for classic lobster rolls and fresh seafood treats. Climb the 252-foot granite Pilgrim Monument for dramatic harbor views, then escape to Race Point Beach to enjoy the sights, sounds and smells of the open ocean.

Eat innovative seasonal dishes at Strangers & Saints and great seafood at Mac’s Fish House , which has crispy fish and chips and Happy Hour dollar oysters. Explore the beautifully barren Outer Cape’s stretch of the Cape Cod National Seashore , including Truro’s picturesque Highland Light .

7.  Ogunquit, ME

Set on the breathtaking Maine coast, Ogunquit is a popular, classic beach town with a quiet ambiance, particularly in the cooler months when crowds disappear. But it’s also a historic arts community; the Ogunquit Museum of American Art was started in the 1950s by native artist Henry Strater, a student of Ogunquit’s Perkins Cove artists colony.

Wander the galleries around town, explore the Barn Gallery on Shore Road and get tickets to a show at the Ogunquit Playhouse —which boasts eight decades of professional theatre and summertime children’s productions—or another summer stock theater.

8.  Watch Hill, RI

A coastal village that’s part of the town of Westerly, Watch Hill has one of the best beaches on the East Coast, and celebrity glamour to spare. Get to town early and take a walk out on the Napatree Point Conservation Area , where  you’ll find the remains of Fort Mansfield and lots of beautiful birds like osprey and piping plovers.

After your nature walk, head into the charming town for a stroll and some shopping. The kids will love the vintage carousel, and be sure to have lunch at the Olympia Tea Room (supposedly Taylor Swift’s fave—you can take a peek at her house from afar, too, because it’s hard to miss). Finish the day with cocktails at the gorgeous Ocean House , where you can have a drink and a bite to eat.

9.  Concord, MA

Stroll to the Old North Bridge and explore the Minute Man National Historical Park’s five-mile Battle Road Trail, dedicated to the Battle of Concord (April 19, 1775), where militia engaged with British troops and ignited the Revolutionary War. The 19th-century Transcendentalist movement and its influential authors and thinkers—Ralph Waldo Emerson, Henry David Thoreau and Bronson Alcott—were rooted in Concord, and the Concord Museum is a good place to connect the dots. Located just outside of Concord Center are Walden Pond , which honors Thoreau’s famed naturalist journal, and Orchard House , where Louisa May Alcott wrote Little Women 150 years ago.

Pick up a picnic lunch at The Concord Cheese Shop . The Saltbox Kitchen’s tasty dishes and small-batch brewery are both fueled by produce from its nearby Saltbox Farm. For dinner, Woods Hill Table  also sources from their own farm at Woods Hill in Bath, NH, and the sleek, seasonally-focused 80 Thoreau is worth the day trip alone.

10.  Providence, RI

Providence is a foodie’s dream. Why does this small capital city have so much kitchen talent? Nearby Johnson & Wales University’s College of Culinary Arts is a major factor. Hemenway’s downtown is the grand dame of area seafood restaurants;  Waterman Grille is a vibrant jewel on the East Side near Brown University; and Aleppo Sweets is a lauded Syrian bakery and cafe—just to name a few spots. Federal Hill, the city’s impressive Italian neighborhood, is also loaded with Italian eateries and shops. 

Waterplace Park is a lovely gathering spot, and it anchors the city’s annual WaterFire program, which runs from spring through late fall; braziers along the Providence River are lit at sunset and stoked with aromatic wood by black-clad figures on boats, while themed music plays.

Providence is home to the notable Trinity Repertory Company , and The Strand Ballroom & Theatre, one of the nation’s best rock venues. The Rhode Island School of Design’s museum includes one the country’s finest university art collections.

11.  Mystic, CT

Settled in 1654, Mystic was once a shipbuilding seaport village. Now, it's a quintessential New England town, packed with mom-and-pop shops and activities for the whole family to do. 

During warm weather, spend a few hours on the sea with a day sail or sunset cruise from Argia Mystic Cruises , or visit the famous Mystic Aquarium or the Mystic Seaport Museum .  

After working up an appetite, stroll through the village to see the famous weighted Bascule bridge . P ick up a sweet treat from award winning Sift Bake Shop  and  splurge on a Connecticut lobster roll at the The Shipwright's Daughter  or a hearty, grass-fed burger at the Engine Room .  And, if you must eat pizza in Mystic, head to Nana’s Bakery and Pizza for inventive takes on personal pies.

12.  Falmouth, MA

Falmouth is nestled on the southwestern part of Cape Cod, 20 miles south of the Sagamore Bridge. Lined with great beaches, cool boutiques and relaxing spots to eat and drink, it's also one of The Cape’s easiest towns to get to. Do breakfast or lunch like a local at The Pickle Jar Kitchen .

The Falmouth Museums on the Green brings 1700s Cape Cod to life; the Federalist home of Dr. Francis Wicks is wonderfully preserved and packed with original artifacts. The Shining Sea Bike Trail ,  which hugs the coast and brings you past lovely views of both the Vineyard Sound and Buzzards Bay, runs from Falmouth to Woods Hole. The trail’s name comes from “America the Beautiful,” the famous poem by Katherine Lee Bates, a Falmouth native. (Though once a railroad, the path follows ancient Wampanoag Indian trails.) One more highlight: the Woods Hole Oceanographic Institution Ocean Science Discovery Center .

13.  Lexington, MA

The best part of taking a day trip to Lexington? You can easily do it by bicycle by traveling down the Minuteman Bikeway , which begins in North Cambridge and runs right through the leafy suburb, some 15 miles northwest of Boston. This posh town is most famous for its historic Battle Green , where the bloody Battle of Lexington took place and patriotic Minute Men engaged the British Army on Lexington Common. Many of the original homes flanking the battleground are preserved, including one that serves as a visitor’s center.

Stroll Lexington Center’s mom-and-pop shops, enjoy homemade ice cream at Rancatore’s or dine at il Casale   from local chef Dante de Magistris, who draws from his family’s roots to make handmade pastas, delicious sfizis and classic dishes, all in a rustic-chic atmosphere. For an elegant Sunday brunch or dinner, The Inn at Hastings Park’s Town Meeting Bistro  is a modern pleasure involving sleek, seasonal dishes.

14.  Kittery, ME

Kittery, while most famous for its shopping, has so much more to offer. First stop: Bob’s Clam Hut , a 60-year-old roadside diner that serves incredible fried clams, sustainable local fish and amazing milkshakes. Next stop? Yes, shopping at the adjacent Kittery Premium Outlets , whose stores include everything from discounted Calvin Klein to Lindt chocolate.

Also known for the historic Portsmouth Naval Yard —which is in Kittery, not neighboring Portsmouth, NH—this sleepy town includes Tributary Brewing Company , which has a cool tasting room and live music on weekends.

The heart of Kittery Foreside, which is the downtown area, is Wallingford Square and it's dotted with all kinds of restaurants including the sleek bistro Anneke Jans  and casual asian eatery  Anju Noodle Bar . Or  stop by Lil’s Café , a quaint spot set in a former bank whose old walk-in safe is now its Vinyl Vault, a small alcove with used records for sale. Lil’s bakery downstairs turns out some of the best pastries in New England and excellent chai, too.

15.  Washington, CT

For a small town in rural Connecticut, Washington has a big reputation for its arts and architecture. The Judy Black Memorial Park and Gardens is set in a once-abandoned gas station and boasts lovely landscaping and revolving art exhibits.

Every July, the Litchfield Jazz Festival takes place at venues around town and world-renowned modern dance company Pilobolus holds its Five Senses Festival . In September, Gilmore Girls fans take over—the town inspired the beloved TV program’s fictional Stars Hollow. Surrounded by colonial architecture, you can shop at unique boutiques and treat yourself to dinner (and a room, for a real spurge) at the historic, luxurious Mayflower Inn .

16.  Stockbridge, MA

Just off I-90, Stockbridge is the gateway to the beautiful Berkshires, part of the Taconic Mountains. Main Street is home to the venerable Red Lion Inn , a one-time frontier town tavern that maintains a casual eatery called Widow Bingham’s Tavern, as well as a gorgeously original main dining room with traditional favorites and an award-winning wine list.

Nature and art dominate the area: Just off Park Street, behind Main Street, take the wooden footbridge and walk the Laurel Hill Association’s beautiful trails. Visit the Norman Rockwell Museum and see where the renowned illustrator and artist lived and worked. Nearby, visit Chesterwood , the home of the Lincoln Memorial sculptor Daniel Chester French, and Naumkeag , a Gilded Age architectural masterpiece. A few miles away in Lenox is the Tanglewood Music Center , the Boston Symphony Orchestra’s summer home. Nearby, you can take a guided tour of Edith Wharton’s home, The Mount , and learn about the woman behind the building and the books.

[image] [title]

Discover Time Out original video

• Press office
• Investor Relations
• Work for Time Out
• Editorial guidelines
• Privacy notice
• Do not sell my information
• Cookie policy
• Accessibility statement
• Terms of use
• Copyright agent
• Modern slavery statement
• Manage cookies
• Advertising

Time Out products

• Time Out Worldwide

• Search Please fill out this field.
• Manage Your Subscription
• Give a Gift Subscription
• Newsletters
• Sweepstakes
• Destinations
• Massachusetts

These Are the 30 Best Things to See and Do in Boston

With historic sights, beloved hometown sports teams, a thriving arts scene, and local brews and bites, you'll never be bored in Boston.

Boston is consistently ranked as one of the top 10 most-visited cities in the United States — and for good reason. Home to a thriving food and drink scene, historic landmarks, and activities for all types of travelers, the city offers plenty to keep visitors occupied. So, whether you're on a solo adventure or traveling with the whole family, here are 30 of the best things to do in Boston.

Walk the Freedom Trail.

The two-and-a-half-mile, self-guided Freedom Trail tour takes visitors through the city, telling the story of the American Revolution with stops at museums, churches, meeting houses, and other historical markers along the way. Do it alone, or find tour options here .

Step back in time at the Paul Revere House.

Want even more Boston history? Head to the Paul Revere House . The home, which was once owned by Revere and sold in 1800, served as everything from a boarding house to a local shop to tenement apartments. Now, it's a museum offering guided tours of the restored home that will transport you back in time.

Stroll through the Boston Common.

The Boston Common is the very heart and soul of the city. First built in 1634, it is the oldest public park in the United States. On the park's 50 acres of land, guests will find the Frog Pond, a softball field, and monuments galore. Take your time strolling through the landscaped gardens and enjoying the sights.

See the animals at the New England Aquarium.

For more than 50 years, the New England Aquarium has invited guests to come and meet a few of the coolest sea creatures on Earth. From penguins to sharks, stingrays to seals, and everything in between, the aquarium has all kinds of animals for curious visitors. It's also a working research aquarium, meaning visits and donation dollars partially go toward ocean conservation and preserving these species for generations to come.

Take the kids to the Franklin Park Zoo.

For even more animal adventures, pay a visit to the Franklin Park Zoo . The 72-acre zoo is the place to be for a red panda, tiger, or zebra sighting right in the middle of the city. There are also plenty of expert-led chats to attend, as well as children's events, making it a place the entire family will love.

Or, see animals in their natural habitat with a whale-watching tour.

Take to the waters outside of Boston for a high-seas adventure like a whale-watching excursion . Hop aboard a tour with the New England Aquarium and Boston Harbor City Cruises to see whales, dolphins, and sea birds on their migration routes — all from a safe distance, of course.

Go for a walk around the Esplanade.

Another worthy place for a stroll is the Esplanade, a three-mile path that hugs the Charles River. It's an excellent spot for a walk or bike ride along the lovely green spaces on the banks of the river, where you can watch boaters. And if you're so inclined, you can donate to the Esplanade Association , a nonprofit working to preserve the space for more than two decades.

Violet Smirnova/Travel + Leisure

Take to the Charles River.

You may feel inclined to get on the water yourself — and you can do just that by joining Community Boating Boston on a sail. The organization offers sailboat, kayak, and stand-up paddleboard rentals for those feeling adventurous.

Watch a midnight movie at Coolidge.

The Coolidge Corner Theater, which first opened its doors during the golden age of cinema in 1933, is already one of the most incredible places to see a movie in the city. But to up the ante, try and visit for one of its After Midnite showings. The late-night programming includes horror films and off-beat flicks, making it great for an after-dark fright.

Visit the Isabella Stewart Gardner Museum.

Isabella Stewart Gardner was a woman who knew what she liked. She was a millionaire, a bohemian, and an intellectual, and the museum bearing her name is a gem of Boston's thriving art scene, with luxurious landscaped grounds. Perhaps some of the museum's most famous works aren't hanging on the walls, though, as eagle-eyed visitors can spot empty frames that once held priceless pieces, stolen from the space in a famed art heist in 1990.

Spend a day at the Institute of Contemporary Art.

The iconic Institute of Contemporary Art is housed in 65,000-square-feet of space, making it a spot where you can easily spend an entire day. The institute includes gallery exhibits, a theater, and a cafe, along with a gorgeous outdoor deck so you can get a breath of fresh air and reflect on all the works you've just seen. Plus, admission to the institute is free on Thursdays after 5 p.m., but make sure to snag your timed ticket in advance.

See the Arnold Arboretum.

The Arnold Arboretum of Harvard University is a living museum of trees and plant life, with a particular focus on flora and fauna from eastern North America and Asia. This National Historic Landmark is open every day and always free for visitors.

Scope out the treasures at The Museum of Fine Arts.

The Museum of Fine Arts is a crown jewel in Boston's museum scene. It includes American works of art and artifacts from around the globe, including pieces from across Europe, Asia, and Africa. The museum also holds collections in photography, musical instruments, textiles, and more.

Swing by Encore Boston Harbor.

Encore Boston Harbor is the place to go if you're looking for some good old-fashioned fun. The entertainment venue, which opened in 2019, includes a hotel, five-star dining options, shopping, and even a casino for those wanting to roll the dice and test their luck. Head out for a meal, stay for a game, and perhaps book an overnight stay so you can do it all again tomorrow.

Shop on Newbury Street.

Visitors to Boston could make an entire vacation out of just strolling down Newbury Street. The famed street is chock-full of boutique shops, restaurants, galleries, and more, so you may have to visit more than once to ensure you've seen and done it all. Keep track of pop-up events on the street's website here .

"Travel" the world at the Mapparium.

The Mapparium may just be the best way to "see" the world without ever leaving Boston. The three-story site is actually the world's largest walk-in globe. Guests can walk through the globe via a bridge dissecting its equator before leaving to check out "Our World: Mapping Progress," an exhibit highlighting "humanity's advancement since 1935."

Root for the Red Sox at Fenway.

There is arguably nothing more iconic in Boston than Fenway Park . If you visit during the regular baseball season, try to get tickets to a game. While inside, cheer for home runs over the Green Monster and get ready to sing "Sweet Caroline" at least once.

And cheer on the Celtics and the Bruins at TD Garden.

Visitors to Boston can continue to root for the hometown team by getting tickets to a Celtics or Bruins game, depending on the season. Luckily, both teams play under one roof at TD Garden , which also hosts plenty of concerts, so check the calendar to see what shows or games you can take part in next.

Grab a good book at the Boston Public Library.

When constructed in 1848, the Boston Public Library became the first large free public library in the nation. It remains a place where visitors can check out a good book or read in the public spaces. The library hosts both tours and regular events, so check its calendar and see what piques your interest.

Grab a bite at Boston Public Market.

The Boston Public Market , a year-round indoor marketplace, hosts nearly 30 New England-based food purveyors and artisans. It's also a place you can feel good about visiting, as it's a registered nonprofit with public impact goals to support "economic development, New England food system resilience, public health and education, affordability, and access."

Drink a local brew at Samuel Adams Boston Brewery.

Boston is home to a thriving craft beer scene, though the best-known spot for brews is popular brand Sam Adams. The company now sells its brews just about everywhere and even allows guests to come and taste its latest creations on a brewery tour. See all tour options here .

Devour dessert with a cannoli from Mike's Pastry.

There are plenty of excellent places to grab a cannoli in Boston's Italian mecca, the North End. Walk into any bakery in the neighborhood and you'll surely be delighted. But if you need a little guidance, we suggest heading to Mike's Pastry . It's the largest bakery in the neighborhood and wildly popular, but for good reason. Just be prepared to wait in line for your sweet treat.

Explore more city history on a walking tour of Chinatown.

In the 1880s, Chinese immigrants to Boston founded their own community, now known as Chinatown. The neighborhood has always played a significant role in the city's history and is a place where visitors can come to both learn and dine to their heart's delight. Hop on a Boston by Foot tour to ensure you see and dig in at all the right spots.

Watch a show at the Boston Ballet.

The Boston Ballet has delighted audiences since the 1960s, with performances ranging from classics like George Balanchine's "A Midsummer Night's Dream" and Mikko Nissinen's "Swan Lake," as well as modern pieces by William Forsythe, Jiří Kylián, Wayne McGregor, and more.

Waddle around on a Boston Duck Tour.

The Duck Tour may not have started in Boston, but the city has certainly perfected it. We'd be remiss not to mention this as a perfect Boston attraction for out-of-town visitors, as it goes to all the best city locations and even right onto the Charles River thanks to the amphibious vehicles. See all tour options here .

Shop and dine at Faneuil Hall Marketplace.

Want to pack as much Boston as you can into a single place? Simply head to Faneuil Hall . The famed marketplace is home to more than 70 retailers across its 200,000-square-foot space, including food, apparel, and specialty gift shops. It's a place to see and do it all, and it's especially magical if you can visit during the holiday season.

Learn something new at the Museum of Science.

Boston's Museum of Science may be one of the most fun spots in the city. It's filled with interactive exhibits that will surprise, delight, and leave you in awe. Head there to learn about the evolution of dinosaurs, see its exhibit on how vaccines work, and much more.

Stop by Trinity Church.

If you love architecture, design, and history, Trinity Church should be high on your list of things to see in Boston. A National Historic Landmark, the church is also considered by the American Institute of Architects to be one the country's top 10 buildings thanks to its Richardsonian Romanesque design and stained-glass windows. The church is open for both worship and tours throughout the week.

Get medieval at Castle Island.

Castle Island is a hidden gem that even locals tend to overlook. We're not quite sure how considering there is an entire castle-like fort hiding in plain sight. The 22-acre "island" isn't actually an island anymore after a small strip of land was added to connect it to shore, but that doesn't make it any less special. Visitors can come to tour the fort, walk the grounds, or head to its trails for a bit of rollerblading or biking.

Pick up new art at the SoWa studios.

Stroll through the SoWa studios and get a glimpse of the fantastic work from the city's artistic community. Visitors can swing by the first Friday of every month for open gallery tours or make an appointment with an artist to get up close to the works before buying.

Related Articles

The Perfect 2, 3 or 4 Days in Boston Itinerary

Last Updated on January 29, 2024

by Audrey Webster

Disclaimer: This article contains affiliate links. That means if you click a link and make a purchase, we may make a small commission. As an Amazon Associate we earn from qualifying purchases. For more information, see our privacy policy.

As one of the oldest cities in the country, Boston is filled with history. It’s a mash-up of cobblestoned streets and historic buildings with modern skyscrapers. There are a few places you cannot miss while spending a few days in Boston, as well as some lesser-known parts of the city we’ll cover here.

As one of the most dynamic and historic cities in the country, there is a lot to do in Boston and so much that you can’t miss. From American history to esteemed universities to excellent museums and fantastic food (there’s more than clam chowder!), Boston has something to offer everyone.

Table of Contents

How Many Days in Boston?

When in the initial stages of planning a trip, many do wonder how many days to spend in Boston in order to do this New England city justice.

With 2 days in Boston, you’re just scratching the surface. Most of the city’s main attractions are clustered together, so you could see a lot in 2 days, but you’re also missing out on some cool parts that make the city unique.

If you have 3 days, you’re in good shape to see all the highlights as well as some lesser-known sites. You’ll be able to strike a balance between visiting historic landmarks and more trendy neighborhoods.

If you’re lucky enough to have 4 days, you can see more of the city at your leisure or use the fourth day to take a day trip to somewhere nearby. There is no shortage of historic sites and beautiful nature just outside Boston. 

Getting To & Around Boston 

You’re most likely arriving in Boston through the Logan International Airport. You can easily hail a cab, take the GO Boston Shuttle, pre-book a transfer or use public transportation to reach downtown.

If you’re visiting from another city or town in New England or even some city further south such as Washington DC or New York , you might arrive on a train or bus. Make sure to find out which train or bus transfers you need to make depending on where you’re coming from. You can view schedules here.

The Massachusetts capital is a very walkable city and it’s not actually that big. In fact, one of the best things to do in Boston is walk the Freedom Trail. Many of the most historic landmarks are located near each other.

Boston is also well-connected via a subway system, known locally as the T. You can easily get around the city using this if you want to reach somewhere a bit further afield.

Alternatively, there is the Hop On/Hop Off Trolley Tour that provides a convenient way to see the city. Taxis and rideshare are both readily available as well. It is also included in the Boston Go City Pass , which will also save you on entrance fees to many of the paid attractions listed here.

2, 3 or 4-Day Boston Itinerary

If you’re spending a few days in the Massachusetts capital, then there are a number of guided tours that you can take to get an overview of the city such as this historical walking tour , this bike tour or this food tour.

Day 1 – Freedom Trail, Museums, Quincy Market & More

Walk the freedom trail.

This 2.5-mile trail covers many of the historical highlights in Boston. You’ll want to dedicate a few solid hours to walking the trail. You can opt to walk the entire thing or a portion of it.

There are also guided tours available such as this 2-hour walking tour , which could be helpful for providing context to the landmarks as you pass them. Here are the landmarks you can expect to see:

• Boston Common & Boston Public Garden
• Massachusetts State House
• Park Street Church
• Granary Burying Grounds
• Boston Latin School/Benjamin Franklin Statue
• Old South Meeting House
• Old State House
• Faneuil Hall
• Site of the Boston Massacre

Paul Revere House

• Old North Church
• USS Constitution
• Bunker Hill Monument

You could spend however long you’d like walking the Freedom Trail and note that it doesn’t cost anything to walk the trail, but there are generally entrance fees for the various sites.

Depending on how long you want to spend, take the time to walk by these places and pick one or two that interest you to plan to visit those places. With that in mind, plan to spend 2-3 hours on the Freedom Trail.

Boston Tea Party & Ships Museum

Veer off Freedom Trail just slightly to pay a visit to the Boston Tea Party and Ships Museum.

The museum is chock-full with historical experts, interactive exhibits, full-scale replica sailing vessels, and historic artefacts to make this monumental event in America’s history come to life. You can pre-book tickets here.

If you have some time to spare, you can watch an award-winning documentary in Minutemen Theatre that depicts the events that led up to the American Revolution. 

Next to the museum, don’t miss the Observation Deck at Independence Wharf, either, where you can get excellent views of the harbor.

Quincy Market

Quincy Market is where old and new seamlessly merge. Here you can find hundreds of shops, both inside and outside the building. The market was established in 1825 and spans three buildings: Quincy Market, South Market, and North Market.

It’s another great place to stop as you’re walking the Freedom Trail to grab a bite to eat or do some souvenir shopping. The market is especially charming during the winter months when it’s decorated for the holidays. Quincy Market was named a National Historic Landmark in 1966. 

Go to a Red Sox game

Go see the “Green Monster” for yourself during your visit to Boston. Even those who wouldn’t consider themselves baseball fans will enjoy seeing a game at Fenway Park.

It’s been the home of the Boston Red Sox since 1912, making it the oldest stadium in Major League Baseball. If you don’t have time to see a game, you can still take a guided tour of Fenway. It’s a great way to wrap up your first day of sightseeing in Boston. 

If it’s not the season for baseball or you don’t care to go to a game, then use this time to stroll along the Charles River Esplanade or, perhaps, visit the nearby Boston Museum of Fine Arts. You could also simply relax in the tranquil surroundings of Back Bay Fens Park.

Day 2 – Boston’s Museums

John f. kennedy presidential museum & library .

This exceptional museum is dedicated to the life and accomplishments of U.S. President John F. Kennedy.

Here, you’ll wander the permanent exhibit that uses large-screen projections, interactive displays, original artefacts, and re-mastered films to learn more about the former president’s life. Consider reserving tickets online in advance to save you time at the door. You can also opt for a guided tour.

A visit to the JFK Presidential Museum & Library is a great way to kick off your second day. 

Institute of Contemporary Art

If you have 2 days, you should consider visiting one of the many local museums. A city that’s so full of history has some great historical museums, but it also has notable art museums like the Institute of Contemporary Art.

Here you’ll find both permanent and rotating exhibits featuring contemporary artists and their work. The museum is located in a beautiful building on the waterfront overlooking Boston Harbor, so you can also take in the view. It’s recommended that you book tickets in advance. 

Isabella Stewart Gardner Museum

This museum is known for its beautiful architecture and courtyard garden. It’s a great museum to visit if you want one that is a little less crowded than other larger museums in the city. Beginning in the late 1800s, Isabella started collecting rare books, manuscripts, and pieces of art to fill her home.

Over the course of her worldwide travels, she acquired art like Rembrandt’s Self Portrait and Titian’s Europa. The museum as it stands today was built in 1901. She lived on the fourth floor and spent the remainder of her life arranging the art throughout its halls.

It’s a unique museum that’s a quiet way to spend the afternoon. If this or any of the other museums don’t interest you, there are plenty of other museums in Boston to take in. For instance, the Museum of Science – located in a building overlooking the Charles River, is an excellent place to visit if you happen to be traveling with children.

Day 3 – Boston Common, Trinity Church, Paul Revere House & More

Boston common.

You might’ve already passed through Boston Common if you walked the entirety of the Freedom Trail. If you didn’t stop for long then, it’s worth your time to dedicate a couple hours to really enjoying the park. Boston Common is America’s oldest public park having been established in 1634 and is located in the Beacon Hill neighbourhood of Boston.

Today, the park is filled with fountains, picnic tables, and green spaces for visitors to lounge and enjoy the day. Make sure to stroll through the adjacent Public Garden, as well, to truly enjoy this urban green space. If you’re seeing Boston in 3 days, then a visit to Boston Common is a great idea.

Trinity Church

When you start exploring Boston, you’ll immediately notice Trinity Church in Copley Square. This historic stone church sits squarely in the middle of downtown’s towering skyscrapers. It’s considered by the American Association of Architects as one of the top 10 buildings in the country.

The parish located there today was founded in 1733, which is more than 150 years before the church was built in 1877. You can enter Trinity Church on your own or schedule a tour with a knowledgeable tour guide to learn more about the church’s history. 

It looks striking as it’s sandwiched between modern skyscrapers like the John Hancock Tower and the Prudential Tower and really symbolises Boston’s mingling of old and new.

Located in the North End neighborhood, the Paul Revere House was the former home of the famous Founding Father Paul Revere. He played a pivotal role in the American Revolution, noted in history books for his famous “midnight ride” to warn colonists that the British were approaching Boston.

The home was built in 1680 and is downtown Boston’s oldest building. Inside, the home is set up to mimic what it would have looked like while Revere lived there. In fact, 90% of the structure today is original material, including doors, windows, flooring, and internal wall material.

You can pop into this Boston museum for a self-guided tour or try to time your visit to see colonial reenactors demonstrate key moments of America’s history. 

If this doesn’t interest you as much or if you’re traveling with children, consider, as well, heading to the nearby New England Aquarium where you can learn all about local marine life or you can take a food tour of North End.

The Museum of Bad Art

You’ve probably never been to a museum that focuses on bad art. The Museum of Bad Art houses “art too bad to be ignored” and is a highlight worth adding to your time in Boston. It’s the world’s only museum dedicated to bad art that began in the basement of a private home.

The museum has since grown into a local favorite that shines the spotlight on quality bad art. It’s a quirky and fun addition to your Boston trip, especially if you happen to be planning a 3-day itinerary. 

Day 4 – Lexington & Concord, Salem or Cape Cod Day Trip

Lexington and concord.

Lexington and Concord is arguably the most famous site of the Revolutionary War. For history buffs, this is a great way to round out your 4 days in Boston. It’s where the first shots of the war were fired.

To reach Lexington, you’ll take the subway and bus for a total travel time of about 45 minutes before getting off at Lexington Battle Green. You can reach Concord by taking the MBTA directly from Boston.

Lexington Green is a good starting point for your visit. This small town is home to the Belfry that sounded the alarm in 1775 to call the militia to fight. Here, you’ll also find John Hancock’s childhood home or Buckman’s Tavern. In Concord, make sure you visit the Old North Bridge.

You can also find Walden Pond, made famous by writer Henry Thoreau, and Louisa May Alcott’s “Orchard House”. There’s a lot to see during a day trip to Lexington and Concord, so make sure you leave early in the day to give yourself ample time. 

You’ve most likely heard of Salem, Massachusetts due to its famous 1692 witch trials. Salem is only about 30 minutes from Boston, so it’s an easy day trip. You can easily reach it by taking the commuter train that connects the cities, a high-speed ferry or an organised day tour.

During your day in Salem, make sure to visit the Salem Witch Trials Memorial, Peabody Essex Museum, the Old Town Hall, and the Witch House. You can end your day with a visit to Winter Island Park and Lighthouse.

As you might’ve guessed, one of the best times of year to visit Salem is Halloween. The little town comes to life with spooky decorations.

Without a doubt, Cape Cod is beautiful, especially in summer. This stretch of coastline is full of charming towns, great seafood, and relaxing beaches.

Cape Cod is about 3 hours from Boston by car, which tends to be a little long for a day trip. Instead, you can take the Cape Cod Fast Ferry from Boston to Provincetown, which is the largest town on the Cape.

In Provincetown, you can enjoy the local art galleries, lounge on the beach, and walk around and enjoy the quaint homes and shops.

If you have more than 4 days in your Boston itinerary, spending more than one day on the Cape is a relaxing way to bring your time in the area to a close.

Where to Stay in Boston

Harborside Inn – This 3-star hotel in downtown Boston is a great choice for mid-range travelers to the Massachusetts capital. There are a number of great rooms to choose from, a wonderful location for exploring the city and plenty of other amenities to enjoy.

Omni Boston Hotel – If you’re looking for luxury while in Boston, then this sophisticated hotel is a great option. They have a range of lovely rooms on offer and an unbeatable location for exploring all this historic city has to offer.

HI Boston – Those visiting Boston on a budget will love this backpacker’s hostel in the center of the city. They have a range of both dorms and private rooms on offer along with other perks and great common areas for guests to enjoy.

Not quite what you’re looking for? Click here to browse more Boston hotels!

The perfect itinerary for Boston is the one that’s packed with what excites you most. If you’re a history buff, you’re going to love it here. Foodies, explorers, and everyone in between will find something to love in Boston.

Are you planning a trip to Boston? Have any questions about this itinerary? Let us know in the comments!

Related Posts:

The Perfect 2, 3 or 4 Days in Cape Cod Itinerary

Martha’s Vineyard vs Nantucket: Which Island to Visit?

17 Best Stops on a Boston to Bar Harbor Road Trip

About Audrey Webster

Audrey Webster is a writer for The World Was Here First. She is an Oregon native who has visited countries across the globe and currently spends her weekends exploring the Pacific Northwest and surrounding states. Her approach to traveling combines exploring famous tourist sites and wandering off the beaten path to discover new destinations.

Leave a Comment Cancel reply

35+ Amazing Day Trips From Boston Massachusetts

Wondering where to go on a day trip from Boston? Boston has always been my most frequent city of travel. I’ve lived there too. Based on my own experience exploring the region, here’s my list of 35 great day trips from Boston.

Boston is perfectly situated in the northeastern region of the United States . This area of New England boasts gorgeous beaches, charming Colonial towns, seaside ports, and destinations steeped in history.

These destinations are all less than 2 hours away from Boston. Any more than 2 hours is just too far afield for a proper day trip.

Because of its central location, Boston makes a great launchpad for day tripping in New England. Boston is well-connected to other towns and cities. Boston’s main arteries (I-90, I-93 and I-95) give you easy access to Maine, New Hampshire, Connecticut, Rhode Island, Western Massachusetts, and even Vermont.

Boston’s main arteries (I-90, I-93 and I-95) give you easy access to Maine, New Hampshire, Connecticut, Rhode Island, Western Massachusetts, and even Vermont.

On a day trip from Boston, you can escape the city’s adoring (and sometimes maddeningly intense) crowds.

Best Day Trips From Boston

Here are my picks for the best day trips from Boston. I’ve given you a whopping 36 options, along with expected drive times. I’ve listed them in alphabetical order for ease of reference.

The options for Boston day trips are endless and incredibly varied. There’s something of interest for everyone, from culture vultures to history buffs to nature lovers.

You can pick what suits you most, whether you want to relax on the beach or explore a cozy New England town.

If pressed to choose, I’d have to say my top three picks for Boston day trips are Portland Maine (cool foodie city), Stockbridge Massachusetts (quintessential New England town), and Portsmouth New Hampshire (adorable arty village).

1. Bristol Rhode Island (1:10 Drive)

Bristol is a beautiful New England town that’s full of history and charm. With a red-white-and-blue painted stripe down Hope Street, it exudes Americana. 

Bristol has everything you need for a relaxing break from Boston — fine dining, bike trails, art galleries, and ocean views. A highlight of Bristol is its well preserved historic architecture. In Bristol, you’ll find Colonial, Federal, and Gilded Age buildings. 

Linden Place Museum features a stunning spiral staircase and movie memorabilia. Blithewold Mansion has immaculately curated gardens, hosts concerts in the summer, and offers dramatic harbor views.

If you like to hike or bike, the East Bay Bike Path will suit. It’s a 14.5 mile paved path connecting Providence and Bristol, which gives you panoramic views of Narragansett Bay.

2. Cambridge Massachusetts (5 minute drive)

The easiest day trip from Boston is to its next door neighbor, Cambridge. Historic Cambridge is a lively university enclave, with the Charles River as its playground and backyard.

Cambridge is home to the renowned Harvard University (where you’ll be wrapped in red brick) and the Massachusetts Institute of Technology (where you can admire eclectic modern architecture). You can book a walking tour of Harvard here and a tour of MIT here .

And it’s not just the universities that dazzle. In Cambridge, visitors can enjoy outstanding museums, a vibrant performing arts scene, and delicious haute cuisine restaurants.

The  Harvard Art Museums  are the best art spot, with a range of works from antiquity to present, including a prized Van Gogh .

Be sure to hang out in Harvard Square, the iconic center of Cambridge. It’s a triangular plaza located at the intersection of Battle Street, John F. Kennedy Street, and Massachusetts Avenue.

You’ll find all manner of humanity — students, tourists, political activists, buskers, chess players, and other street creatures.

You can also visit  Longfellow House . It’s located on Brattle Street, the historic road connecting old Cambridge and Watertown.

The house museum is famous as the one time home of Henry Wadsworth Longfellow. He was a novelist and poet who wrote stirring tales that thrilled 19th century America, including the  Midnight Ride of Paul Revere .

3. Cape Elizabeth Maine (2 Hour Drive)

Cape Elizabeth is gorgeous little town just south of the city of Portland. The town faces out into Casco Bay.

People have lived in Cape Elizabeth for thousands of years. In 1765, Cape Elizabeth officially became a town. For a glimpse of those early days, stop by the  Spurwink Meeting House . The austere white clapboard church was built in 1802.

The town’s stretch of coastline is stunning, dotted with lighthouses. The cliff walk is a lovely must do experience in Maine.

The 19th century Fort Williams Park in Cape Elizabeth guards the entrance to Portland. It’s home to the Portland Head Light. You can walk the park’s Arboretum trails, enjoy a picnic, or explore the fort’s old batteries.

3. Charlestown Massachusetts (5 minute drive)

Charlestown is Boston’s oldest neighborhood. It’s just across the river from the North End.

If you’ve walked the Freedom Trail in Boston, you’ve already been to Charlestown. The town is home to the Bunker Hill Monument and the USS Constitution, which are must visit landmarks in Boston .

In 1775, Charlestown was the site of one of the most important battles of the Revolutionary War. American patriots defeated the British in the Battle of Bunker Hill. Nearly the entire town was destroyed during the battle and it wasn’t rebuilt until after the war ended.

Nowadays, Charlestown is a pretty place that’s well worth a stroll. A sense of Colonial charm permeates the streets and parks of Charlestown. The town has a classic main street, town square, and pretty clapboard homes.

4. Chatham Massachusetts

A visit to Cape Cod is a no-brainer day trip from Boston. But where to stake your claim?

Try the inimitable charms of Chatham, a tony New England town. In Chatham, the homes induce jaw drops, the historic center is walkable, and the seafood is hauled in just offshore.

Chatham’s curving Main Street conjures up low key elegance and old world charm. Chatham is the only Cape Code town bounded on three sides by water. It’s consistently ranked as one of the US’ best beach towns.

Chatham Lighthouse Beach is considered the most scenic public beach. It’s set beneath Chatham’s iconic lighthouse. This wild stretch of the Atlantic is the place for long walks and sunbathing (the surf is rough).

If you need a dose of culture with your beach retreat, head to the Orpheum. It’s a restored vintage theater showing first run movies and classics.

Or, take in a play or musical at the Monomoy Theater, after browsing the casual to high end shops.

5. Concord Massachusetts (35 Minute Drive)

Just 15 miles north of Boston is the small town of Concord. It’s the perfect Boston day trip for literary buffs. Concord is a steeple-studded town home to pretty  Walden Pond . Walden Pond is a nature preserve that’s home to countless local flora and fauna.

Walden Pond is forever linked to novelist Henry David Thoreau. From 1845 to 1847, he lived in a one room cabin , the property of his friend and mentor Ralph Waldo Emerson. A replica of the original cabin is about half a mile from Concord.

There, he wrote one of America’s most famous novels,  Walden  or  Life in the Woods.   Walden  explored simplistic living, solitude, and harmony with nature.

In Concord, you can also visit Emerson’s House and Louisa May Alcott’s Orchard House . The novelist based  Little Women  on her experiences growing up in this house with her sisters.

Today, the historic home is a museum. It has 80% of its original period furniture.

You can tour the kitchen, dining room, parlor, art studio, and the bedrooms. Louisa’s bedroom has the small white desk where she penned  Little Women  and other books.

If you want to learn about Concord’s Revolutionary War and literary legacy, visit the Concord Museum . On display, you’ll find Native American artifacts, Thoreau’s snowshoes and furniture, Ralph Waldo Emerson’s study, Paul Revere’s original signaling lantern, and period collections of decorative arts and furniture.

If you want to pay homage to Concord’s famous authors, visit Sleepy Hollow Cemetery. You’ll find the final resting places of Thoreau, Emerson, Alcott, and William Ellery Channing.

6. Concord New Hampshire (1:10 Drive)

Concord is the capital of New Hampshire. It’s a sleepy New England town that I used to spend parts of the summer in. Founded in 1734, Concord embodies the American spirit. There are a fair number of things to do in Concord.

You can visit the New Hampshire State House, built in 1819. It sports a gleaming eagle topped gold dome, reminiscent of Boston’s own state house. The New Hampshire legislature still uses the original chambers.

Just steps from the capitol is the New Hampshire Historical Society. It boasts a sculpture by the famous Daniel Chester French.

You can also visit Pierce Manse, the former home of President Franklin Pierce. Via a guided tour, you can see period artifacts. Franklin’s grave is also in town.

7. Essex Connecticut (2 Hour Drive)

Essex just exudes small town charm. It has a bucolic setting on the banks of the Connecticut River. The town is consistently rated as one of America’s best small towns.

Essex seems halted in time, looking much as it did during the height of its ship building prosperity. Essex has a picture perfect harbor. It’s scattered with charming inns and historic architecture.

On Main Street, whitewashed houses jostle side by side, in early Colonial and Federal styles. Pop into the Griswold Inn, especially for its vaunted Sunday breakfast. The cute shop Good and Curiosities sells gifts with a historical theme.

Essex is famed for its riverboat tour, the Essex Steam Train & Riverboat. On a 2.5 hour tour, you can travel by train and boat through the countryside. By boat, you’ll glide by farms, inlets, coves.

8. Exeter New Hampshire (1 Hour Drive)

Exeter was founded in 1638 by Reverend John Wheelwright. This pretty new England town brims with charm at every turn. The beauty of Exeter will appeal to everyone from art lovers to history buffs to recreational seekers.

You can take a leisurely stroll in the quaint and historic downtown. You’ll find elegant buildings with shops, restaurants, art galleries, and more.

Or, walk down tree-lined streets to discover historic homes, including the Ladd-Gilman House that’s now the  American Independence Museum .

If you want to experience the great outdoors, Essex has hiking, biking, and water sports. During New England’s fall foliage season , the colors are truly breathtaking.

9. Hanover New Hampshire (2 Hour Drive)

As a graduate of Dartmouth College, Hanover is a sentimental favorite of mine. And it clocks in at 2 hours, my limit for day trips from Boston.

Forbes named Hanover one of America’s Prettiest Towns. For a remote rural town, Hanover packs a surprising cultural punch.

The best place to get your art fix is the wonderful Hood Museum of Art . It’s one of the oldest teaching museums in the country. It has a large collection of artifacts and art dating back to Assyrian culture in 900 BC.

But it’s not all ancient. The museum has a surprisingly good collection of contemporary art, with works by Rothko and Ed Ruscha. It also showcases contemporary African and Native American art.

You should also pop into Baker Library. You’ll find eye catching murals by Jose Clemente Orozco in the reading room.

Hanover is also home to the Hopkins Center for Performing Arts (the “HOP”). There, you’ll find a wide variety of performing arts — plays, shows, concerts, special events, movies, etc.

Here’s my itinerary for spending  one day in Hanover . In addition to just driving to Hanover, you can take the Dartmouth Coach from Logan Airport.

10. Hartford Connecticut (1:35 Drive)

Hartford is one of the oldest cities in the United States. It makes a great day trip from Boston if you want to visit another city. The capital of Connecticut is home to historic sites, art museums, and beautiful parks.

It’s also the birthplace of Mark Twain, a culinary powerhouse, and home to one of the best “little downtowns” in New England.

The Mark Twain House & Museum is a national historic landmark. The museum has it all: inspiring architecture, gorgeous interior design, lovely grounds, and fascinating stories about its owners. It offers visitors an opportunity to learn about the novelist Mark Twain, his family, and his legacy.

Another good reason to visit Hartford on a day trip from Boston is to visit the magnificent Wadsworth Atheneum Museum of Art . The castle-like museum is one of the best museums in New England .

The Wadsworth first opened its doors in 1844. It’s since grown to a collection of over 50,000 works of art from over 5,000 years. There are significant works of modern and contemporary art.

You’ll find works by Frans Hals,  Caravaggio , Orazio Gentileschi, and Bernardo Strozzi. There’s a beautiful painting by pre-Raphaelite artist William Holman Hunt called  The Lady of Shallot . There’s also an American art collection, with works by John Singleton Copley and Charles Wilson Peal.

11. Keene New Hampshire

Keene is a beautiful hidden gem in New England’s Monadnock Region. A lively college town, Keene combines culture and the great outdoors.

Keene offers stunning brick streets, charming maple farms, and quaint specialty shops. Keene even has a white clapboard church with a soaring steeple, the United Church of Christ.

Keene is also home to one of the loveliest and widest main streets in New Hampshire. The historic downtown area is centered on Central Square. It’s an eclectic mix of old time shops, bookstores, and funky craft stores.

Keene is also home to covered bridges and museums. The Horatio Colony House and Nature Preserve is housed in a 1806 Federal style building. The museum houses historical artifacts for the history buff. The nature preserve offers miles of hiking trails for the nature lover.

12. Kennebunkport Maine (1.5 Hour Drive)

Kennebunkport is a classic beauty, one of the most beautiful towns in New England . It’s effectively the Hamptons of the Pine Tree State, known for its dramatic mansions. To see them, take a drive between Kennebunkport and its sister town Kennebunk.

Kennebunkport has a lively downtown, the epicenter of which is called Dock Square. It’s chock full of restaurants, boutiques, and art galleries.

There are plenty of patio cafes for people watching perches. The Clam Shack serves up fried claims and lobster rolls.

For a walking tour of Kennebunkport’s historic buildings, start at the Brick Store Museum on Main Street. Head south and you’ll see several extraordinary structures from the 18th and 19th centuries, including Lexington Elms, Horace Porter House, and Benjamin Brown House.

Summer Street is also an architectural showcase, with an array of Federal and Colonial buildings. To get the complete scoop, you can take a guided 90 minute tour of Kennebunkport’s National Historic District. Buy tickets at the Brick Store Museum.

If you want to hit the beach, try Gooch’s Beach along the Victorian-lined Beach Avenue. Or drive 10 minutes north to the beautiful 3 mile long Goose Rocks Beach.

If you’d like to take a day tour from Boston, this excellent tour combines history and lobster. If you’d just like a guided walking tour once you’ve arrived in Kennebunkport, click here for a 2 hour historic tour.

13. Kittery Maine (1 Hour Drive)

The small town of Kittery is just a short drive from Boston. It’s located on the border between Maine and New Hampshire and is linked by bridges across the Piscataqua River.

Kittery was once known for its shipbuilding. Nowadays, people day trip to Kittery from Boston mostly for its shopping. Kittery has both outlet malls and boutique craft shops. You’ll find stores like Crate and Barrel, Le Creuset, Lululemon, Under Armour, and Nike.

If the weather is warm, head to the beach for a swim. Seapoint Beach is a picturesque shoreline perfect for a dip or a stroll.

You can also visit Fort McClary State Park . It’s a unique historic site that was formerly a defensive military fortification. It has stood for over 275 years protecting the mouth of the Piscataqua River at the entrance to Kittery.

14. Lenox Massachusetts (2 Hour Drive)

Lenox is the perfect day trip from Boston for art lovers. It’s a pretty town of art galleries and upscale boutiques housed in historic buildings.

You’ll find iconic properties like Blantyre, Wheatleigh, Canyon Ranch, and The Mount. At one point, there were so many lavish summer homes that Lenox was known as “the inland Newport.”

In 1902, Edith Wharton, the first woman to win the Pulitzer Prize in Literature, built  The Mount . It was a stately country retreat for the literary lioness and her then-husband. The Mount was modeled after European mansions, but lacked without their ostentatious excesses.

The Mount is home to a summer lecture series, weekly bird walks, concerts, theater performances, and outdoor sculpture exhibits. Edith Wharton’s library has been returned to the house, with 22 first editions of her work.

Lenox is also home to  Tanglewood , the summer home of the Boston Symphony Orchestra. Tanglewood is a must do for music lovers. You can hear symphony orchestras, solo performances, and world class musicians.

15. Lexington (30 Minute Drive)

If you’re a student of U.S. History, Lexington should ring a bell. In 1775, the American Revolutionary War started in Lexington and nearby Concord. Lexungtin is the best day trip from Boston to immerse yourself in Revolutionary war history.

Lexington has more than 10 historic battle sites, cemeteries, and memorials that you can tour. You can see the site of the first battle of the Revolutionary War.

A renowned statue by sculptor Henry Hudson Kitson marks  Battle Green , where the Colonial Minutemen clashed with British troops. In Minuteman National Historical Park, you can see a multimedia exhibit on the Road to Revolution .

While waiting for the British, the Minutemen and their commander, Captain Parker, gathered in the  Buckman Tavern . The interior is preserved exactly as it appeared in the 18th century, complete with the original seven foot wide open fireplace. The old front door still contains British musket-ball holes.

Wrap up your tour of Lexington by seeing the Lexington Depot historic train.

16. Madison Connecticut (2 Hour Drive)

Madison is a shoreline town only East Coasters know about. This beautiful New England day trip from Boston proves the adage that good things come in small packages.

With a population of only 18,000+ residents, Madison delivers a major dose of quintessential New England charm. During his time at Yale, Bill Clinton was so taken with Madison that he mentioned it in his memoir,  My Life , calling it “especially old and beautiful.”

One of the main draws of Madison is Hammonasset Beach State Park . There you’ll find two miles of beaches, wetlands, woodlands, and a nice boardwalk.

The town itself is charming and pedestrianized, full of shops and cafes. A popular haunt is RJ Julis Booksellers, one of the nation’s finest independent shops for book nerds looking for the perfect read.

Madison is also a culture-filled hamlet. A fun outdoor activity is walking the Sculpture Mile . Created by the Hollycroft Foundation, it offers a unique museum-like exhibition that features art work by some of the nation’s most significant sculptors.

17. Manchester New Hampshire (1 Hour Drive)

You might think New Hampshire is all mountains and lakes. But it also boasts a rich cultural history. In particular, Manchester has some fine art offerings that merit a day trip from Boston.

Manchester is home to the state’s only fine art college, the New Hampshire Institute of Art. It also has an internationally acclaimed museum, the  Currier Museum   of Art .

The museum’s permanent collection includes works by Picasso, Monet, Rothko, Wyeth, and O’Keefe. It hosts touring exhibitions. The museum also manages Zimmerman House, designed by architected  Frank Lloyd Wright . It’s the only Wright house open to the public in New England.

Manchester also has a premiere contemporary arts gallery, the Gallery of the New Hampshire Art Institute. It’s multi-functional, serving as an art center, lecture hall, and performance theater. On display you’ll find a diverse mix of traditional and modern art forms, from photography to installation art.

18. Mystic Connecticut (2 Hour Drive)

Mystic is calm and exquisite, a charming waterfront town set on the shores of the Mystic River. It’s quaint downtown is filled with boutiques, galleries, and eateries.

On Main Street, you’ll find Mystic Pizza , made famous by a kitschy 1980s movie. Mystic’s main landmark is Bascule Bridge, the most photographed bridge in Connecticut and a perfect spot for river views.

Mystic Seaport is Connecticut’s #1 attraction, an example of “living history.” It covers 19 acres along the Mystic River.

There are indoor and outdoor exhibits, including four vessels that are National Historic Landmarks. You can climb aboard or peruse the recreated village.

19. Newburyport Massachusetts (1 Hour Drive)

First settled in 1635, Newburyport is an immaculate seaside town. It has a classic New England feel — with red brick streets, lobster shacks, and cobbled lanes. Plus, “the Port” is only 35 miles from Boston, making it the perfect day trip or weekend getaway.

State Street is the heart of Newburyport. You’ll find an eclectic treasure trove of shops — clothing boutiques, bookstores, cafes, and vintage shops. The Firehouse Center for the Arts is Newburyport’s cultural hotspot, offering concerts, musicals, and plays.

When you tire of shopping, surf and sand lovers can hit the beach. Plum Island is only a 20 minute drive from Newburyport.

Plum Island has beautiful and beloved sandy beaches and dunes. And it’s home to the Parker River National Wildlife Refuge, a hidden gem sanctuary with prime bird watching opportunities.

20. Newport Rhode Island (1.5 Hour Drive)

Just two hours south of Boston lies the tony coastal town of Newport. Founded in 1639, Newport is a treasure trove of historic European-style mansions set against ocean views.

Think the Gilded Age’s Astors, Vanderbilts, and Kennedys — families who built the first palatial mansions in the US. Newport is a fancy place.

Most of the mansions are on Bellevue Avenue and a few are on the waterfront. Built by Cornelius Vanderbilt, Breakers Mansion is Rhode Island’s #1 attraction. It’s located on the scenic 3.5 mile Newport Cliff Walk .

If you’d like to tour the magnificent mansions of Newport, this is an excellent day tour from Boston .

The Newport Art Museum is the core of the creative community. The Artists’ Open Space serves up local and regional shows year round.

There’s a dozen commercial galleries in town as well. Island Art is the best, noted for its contemporary pieces.

On the performance arts side, Newport really excels. It offers up everything from Shakespeare plays in Queen Ann Square to musical festivals dedicated to jazz, classical, and folk music in July and August. There’s also the Newport Fine Arts Festival in September.

21. Old Sturbridge Village Massachusetts (1 Hour Drive)

Old Sturbridge Village is a living history museum located in Sturbridge Massachusetts. The museum recreates life in rural New England as it was during the 1790s through 1830s. 

There’s a working farm with heritage breed animals, historic buildings, and horse drawn sleighs. Costumed historians are very engaging and will regale you with historic tales.

You can walk the village and meet the skilled craftsmen who still practice their trade. You can also take a wagon ride. The Village offers several events throughout the year — Winter Photo Walk, Sunday Brunch, and Dinner in a Country Village.

22. Ogunquit Maine (1:30 Hour Drive)

Feeling like a beach day? Nestled along the coast, tiny Ogunquit has been a resort village since the 19th century.

The word Ogunquit translates to “beautiful place by the sea.” You can see why immediately. Ogunquit is like a mini Provincetown. 

The town is a popular summer beach destination in New England, and I came here often as a child. Ogunquit has two beautiful long beaches, Ogunquit Beach and Footbridge Beach. Footbridge is the quieter of the two beaches.

Ogunquit is most renowned for its coastal path, the Marginal Way . It’s a paved 3 mile seaside stroll, starting at Ogunquit Beach and meandering to Perkins Cove.

Perkins Cove is a tiny artisans village, filled with sea-weathered buildings, where you’ll find some art galleries and seafood eateries.

23. Northampton (2 Hour Drive)

Just under 2 hours from Boston, the rural town of Northampton is a cultural nerve center in New England. It’s a pretty town, ringed by 5 colleges and college museums.

Grand mansions line tree-shaded streets. The beautiful Main Street is filled with with shops, art galleries, bookshops, etc.

In downtown Northampton, there are more than a dozen visual arts venues. The Northampton Center for the Arts offers poetry readings, film screenings, and concerts. The Calvin Theater is the premiere concert venue, hosing major touring music and comedy acts.

Four of the five colleges near Northampton offer theater and visual arts. Smack in the middle of Northampton is Smith College. Its beautiful  Smith College Museum of Art  just received a $35 million makeover. The museum offers a year round series of art lectures, contemporary art exhibitions, and films.

Just down the road is  Mount Holyoke College Art Museum . It offers contemporary and traditional exhibitions year round.

You can also admire contemporary work at Amherst’s Mead Art Museum or check out national and international exhibits at Amherst’s University Gallery.

Northampton has a good foodie scene too, with both great pizzerias and haute cuisine. There are two dairies nearby, so the town’s cheese and ice cream options are among the best in New England.

24. Peterborough New Hampshire (1:30 Hour Drive)

Peterborough is a charming New Hampshire hamlet set along the Contoocook River. Peterborough is rich in art and culture, with a charming downtown centered on Depot Square. Thornton Wilder’s Pulitzer Prize winning play,  Our Town , was based on Peterborough.

Peterborough has two theater groups and a renowned artist colony, The MacDowell Colony. The colony is the oldest artist’s retreat in the US, hosting many exhibitions. 

In 1997, it was awarded the National Medal of Arts. Peterborough is also known for its antique shops and galleries.

Nature lovers can head to Miller State Park , which has several trails (and a road) leading to the summit of Mount Monadnock. Edward MacDowell Lake has trails as well, in addition to a beach and boat ramp.

25. Plymouth (45 minutes)

Situated at the mouth of Cape Cod Bay, Plymouth is a historical haven for Boston day trippers. The town was the very first permanent settlement by Europeans north of Virginia. Today, it’s a thriving small town with a lovely historic district, perfect for history buffs.

After parking, first head to the  Mayflower II . It’s is a full scale replica of the original 17th century Mayflower.

The Mayflower is famous as the ship that brought pilgrims to the US in 1620. You can even take a tour of the ship itself, which is docked in Plymouth Harbor

Also, to learn the pilgrims’ tale, stop in the state’s oldest museum,  Pilgrim Hall . There, you’ll find an unmatched collection of ancient artifacts and possessions of the pilgrims. Afterwards, you’ll get to wander around historic  Howland House  and visit the 18th century Court House.

If you want to really step back in time, head to  Plimoth Plantation . It’s a living museum that aims to explore the daily lives of the Colonial Americans. The village has been carefully recreated, with thatched roofs and giant open fireplaces.

The actors in the museum are in period costume and never step out of character. You can watch them performing 17th century tasks including building, gardening, and military exercises.

26. Portland Maine (1:45 Hour Drive)

 Located on a peninsula jutting into Casco Bay, Portland is a rare metropolis in a state filled with small hamlets. It’s a hip and laid back place that almost seems too cool for one of  New England’s most beautiful towns . Portland is a great day trip from Boston for foodies.

Portland has myriad cultural offerings and is a bastion of historical preservation. The restored Old Port is a warren of cobbled streets with a movie set feel. This area is filled with vibrant Victorian buildings and buzzing farm to table eateries.

Start on Commericial Street, the main drag, and work your way inward. The Old Port is known for its cobblestone streets, 19th century brick buildings, and fishing piers. It’s also a hive of activity.

In downtown Portland, there’s a thriving art school, infusing the city streets with creative types. And there are 24 commercial art galleries.

Opened in 1983, Portland’s crown jewel and premiere art destination is the  Portland Museum of Art , an architectural masterpiece designed by I.M. Pei of  Louvre  fame. Its innovative architecture allowed curators to redefine the art viewing experience.

Restaurants and coffee bars are filled with visual art. In June, the revived downtown hosts the Old Port Festival, described as “part freak show, part art festival, part fashion parade.”

Portland is also a hot spot for restaurants, coffee shops, and entertainment. Did I mention breweries? Beer lovers will be happy to know that Portland has 18 breweries all its own. It’s the Craft Bew Capital of America.

If you want to delve more deeply into Portland’s foodie culture, there are some awesome tours.

This tour takes you on a culinary walking tour of the Old Port and this tour lets you feast on seafood in the Old Port. If you’re a fan of craft beer, this tour gives you a taste of Portland’s amazing brew pubs.

27. Portsmouth New Hampshire (1 Hour + Drive)

The New Hampshire town of Portsmouth has also made an appearance on Forbe’s list of America’s Prettiest Towns. Portsmouth is a small town in southern New Hampshire along the Piscataqua River. 

Portsmouth is a great Boston day trip destination for art lovers and foodies. It’s known for its upscale farm to table eateries and art galleries.

Portsmouth’s funky downtown is adorable, with activity centered on Market Square. You’ll find classic white steepled churches, rustic brick shops, and sidewalk cafes. Portsmouth Book & Bar combines books, coffee, and live events.

History lovers should check out the Strawbery Banke Museum . It’s a 10 acre outdoor museum featuring period gardens, preserved historic buildings and detailing the story of how the Portsmouth settlement was founded. 

There are 39 historic buildings dating from 1695 to 1820. The Goodwin Mansion is the most impressive.

Prescott Park is a waterfront park near Strawberry Banke, which is great place to picnic. Enjoy the gardens and the Prescott Park Arts Festival, featuring concerts and foodie events.

in 2017, Travel & Leisure called Portsmouth the “Christmas Capital of North America.” It’s a wonderful New England Christmas destination. “Vintage Christmas” is a month long celebration kicking off December 1. A trolley does a loop of the downtown and a candlelight stroll is held on weekends.

Here’s my guide to the best things to do in Portsmouth in one day .

28. Providence Rhode Island (1 Hour Drive)

Nicknamed the “cooler city” by GQ, Providence is one of the  best towns on the East Coast . Providence is home to an Ivy League college, design schools, and a culinary institute. 

The city is a hodgepodge. It combines big city sophistication with small town charm. It has a vibrant local culture, celebrated restaurants, and sparkling waterfront parks. Providence is full of historic Yankee monuments, but also has a young and funky vibe.

Providence is an easy day trip from  Boston , less than an hour away. But this little jewel box of a city is often overlooked by travelers and definitely underrated. So much the better for its admiring visitors.

Be sure to explore Providence’s Little Italy on Federal Hill. Then, head to the East Side to encounter Providence’s Colonial past. Benefit Street is a bucolic 1.2 mile walk that’s an architectural showcase.

You’ll see some of the most beautiful Federal era architecture in the United States. You’ll also find the lovely campus of Brown University.

And you can’t leave Providence without visiting the fabulous  Rhode Island School of Design Museum . A major cultural institution in the United States, RISD houses over 100,000 works. It’s one of the best small museums in the world .

READ: 1 Day Itinerary For Providence

29. Provincetown Massachusetts (2 Hour Drive Or Ferry)

Do you want to combine a day at the beach with great art? head to Provincetown. The pretty town is tucked away on the far end of Cape Cod.

It’s been attracting artists and creative types for more than a century. Eugene O’Neill wrote his first play here. Modern art luminaries like Helen Frankenthaler, Marsden Hartley, and Hans Hofmann had studios here.

Nowadays, there are 60 art galleries scattered down Provincetown’s picturesque streets. It’s the perfect place for art lovers on the East Coast.

The town’s premiere art venue is the Provincetown Art Association and Museum on Commercial Street. The museum highlights local and New England artists with single artist and themed shows.

The Schoolhouse Center for Art & Design is home to several galleries as well. The Silas-Kenyon Gallery focuses on contemporary art. If you like vintage photography, head to the Driskel Gallery.

The big ticket art festivals you should have on your radar are the Spring Arts Showcase Weekend in May and the Fall Arts Festival in September and October. There’s also an International Film Festival in June.

Don’t forget to eat some lobster, preferably at the Lobster Pot . You can go wine tasting at  Truro Vineyards  or sip craft beers at the  Provincetown Brewing Company .

If you visit Provincetown in the summer, you could spend hours in traffic at the Sagamore Bridge if you drive. But you can also take the Providence Ferry . The fast ferry runs direct from Boston to Provincetown from mid-May through mid-October. It’s only 95 minutes each way.

30. Rockport Massachusetts (55 Minute Drive)

I f a stunning seaside town is on your Boston day trip agenda, head to Rockport. This little town is on Cape Ann, the “other” cape in northeast Massachusetts. There’s a reason why North Shore residents treasure Rockport as a lovely weekend getaway.

There are plenty of things to do in Rockport. Stroll around and admire all the fishing boats and painted cottages. Check out the shops and art galleries on Bearskin Neck, a cute area perched on the edge of town.

Sample some fudge at Rockport Fudgery , eat lobster rolls, relax on the beaches, or take a walk along the rocky coastline at  Halibut Point State Park . You can even go on a  Cape Ann whale watch .

31. Rye New Hampshire (1:10 Hour Drive)

Another good beach option is Rye. The picturesque town of Rye is home to the best beach on the 18 mile long New Hampshire shoreline.

First settled in 1623 on Odiorne Point, Rye is the birthplace of New Hampshire. Rye is largely undeveloped because it’s subject to strict zoning laws.

Rye is a serene contrast to the more frenzied Hampton Beach down the road. In Rye, the tide is small and rolling. It’s a perfect place for a beginner surfer.

You can also take a scenic drive down Route 1A past Millionaire’s Row and ogle at Rye’s breathing early 20th century mansions.

32. Salem Massachusetts (45 Minute Drive)

Even if you haven’t traveled in Massachusetts , you’ve probably heard of Salem. Known as the “Witch City,” Salem is a beautiful seaside town and an easy day trip from Boston.

In Salem, you can learn about Salem’s creepy past as the “witch capital” of the United States. Salem embraces its notorious past, when the infamous 17th century Witch Trials defined the town.

Salem is replete with whimsical magic shops, all things haunted horror, and ghostly tour options. Many of Salem’s top attractions are devoted to its witchy history. This means that the best time to visit Salem in during Halloween.

Salem is also famous for its beautiful 17th century Colonial and Georgian architecture and delicious seafood. Essex Street is the historic cobblestoned district, with the original brick  Old Town Hall .

Old Town Hall dates from 1816. The second floor still stands as a public hall and the first floor is used as a public art space.

If you’re a literary fan, you should visit the  House of the Seven Gables . Built in 1668, it’s one of the oldest Colonial mansions still standing in the United States. Nathaniel Hawthorne immortalized the house in his 1851 novel of the same name.

Inside, you’ll find a recreation of the secret staircase from the novel. The house where Nathaniel Hawthorne was born is also on the property.

Click here to buy ferry tickets to Salem.

There are some excellent guided tours in Salem. If you’re a history buff and want to take a witchcraft trials walking tour, this is an excellent guide . If you’re staying overnight in Salem, you can also take this haunted history nighttime tour or this ghosts of Salem walking tour .

33. Stellwagen Bank National Marine Park (30 Minute Drive)

Want to view some of the most massive animals on the planet? The  Stellwagen Bank National Marine Park  is one of the best whale watching spots in the entire world. It’s a wild ocean destination not far from Boston, just 37 miles away.

The sancturay has an extremely productive and diverse environment, which encourages a wide mix of marine wildlife.

Each summer, around 50 recognized humpbacks return. You can also spot dolphins and seals. There are plenty of whale spotting tours available in the area departing from Gloucester or Provincetown. Click  here  for a list of boat tour operators.

34. Stockbridge Massachusetts (2 Hour Drive)

Stockbridge is the quintessential New England town. It’s one of my favorite day trips from Boston.

Stockbridge was settled in 1734 by British missionaries. It’s blessed with simple charm and a fabulous line up of cultural attractions.

Three of the greatest American artists and authors called Stockbridge their home — Edna St. Vincent Millay, Herman Melville, and Norman Rockwell. One of America’s greatest treasures is the  Norman Rockwell Museum .

Rockwell was one of the greatest artists and illustrators in American history. Stockbridge was Rockwell’s long time residence and what he called his “best studio yet.”

You can also visit  Chesterwood , the home of Daniel Chester. It’s a 1920s Colonial Revival house.

It comes complete with the soaring studio of the legendary sculptor and landscape architect. Chester created the statue of President Lincoln seated in the Lincoln Memorial in Washington D.C., and you’ll see plaster models in the museum.

Every summer, Stockbridge (along with Lenox) hosts the Tanglewood Music Festival. It’s a series of concerts across all musical disciplines.

Stockbridge is also home to one of the Berkshires Gilded Age “cottages,”  Naumkeag . You can tour this quirky 44 room mansion designed by Stanford White, a famed starchitect of the time.

 35. White Mountains, New Hampshire (2 Hour Drive)

It’s a hike to get to the White Mountains from Boston. But it’s worth the long drive to spend a day immersed in nature.

The White Mountains are New Hampshire’s premiere attraction. It’s the best day trip from Boston for fall foliage .

The White Mountains are incredibly beautiful, with plenty of natural wonders. They’ve long attracted vacationers, photographers, and adventurous hikers and skiiers. Mount Washington is the Northeast USA’s peak of superlatives. 

The sinuous Kancamagus Highway in the White Mountains is the granddaddy of New England drives. It’s a scenic 35 mile stretch of highway. You’ll be dazzled by the incredibly unspoiled scenic views along the way.

There a few pullouts for trailheads, providing great photo and hiking opportunities. Continue east until you hit the Rocky Gorge Parking Lot. Here, you can take a walk along the Swift River and get views of the beautiful Falls Pond.

 In Crawford Notch State Park , you can explore the backroads and revel in the beautiful fall colors. If you’d like to do some hiking, there are 35 hiking trails of varying difficulty.

Don’t leave without experiencing the  Mt Washington Cog Railway . It’s a historic train ride up to the summit of Mt. Washington. The mountain is the tallest one in the northeastern United States at 6,289 feet.

Aside from driving around soaking up the scenery, you can explore the cute downtown of North Conway, relax at  White Lake  in Tamworth, do a canopy tour at  Bretton Woods , go on a  waterfall hunt  near Conway. 

36. Worcester (1 Hour Drive)

Right in the heart of Massachusetts, Worcester is one of the best day trips from Boston. Worcester is the second largest city in Massachusetts after Boston. It’s just an hour away from Beantown.

Once in Worcester, take a gander through the huge exhibitions at the  Worcester Art Museum . You can easily spend a good few hours inside. The museum has works of Impressionism, Roman mosaics on the Renaissance Court floor, medieval armor, and Paul Revere’s silver collection.

Be sure to visit the  Bancroft Tower . On the National Register of Historical Places, it’s been around in Worcester since 1900. This fantasy medieval castle was built on a whim to honor a US Navy pioneer. It’s a miniaturized castle in the middle of a park.

At night, you can take in a theater or music performance at the elegant Hanover Inn, Mechanics Hall, or Tuckerman Hall.

I hop you’ve enjoyed my guide to the best day trips from Boston. You may enjoy these other New England travel guides:

• 3 day itinerary for Boston
• 1 day in Hanover New Hampshire
• 35 Landmarks in Boston
• 10 day itinerary for New Hampshire
• Berkshires Road Trip Destinations
• Hidden Gem Towns on the East Coast
• 10 day itinerary for coastal Maine
• 7-10 day itinerary for Vermont
• One week itinerary for southern New England
• Fall foliage road trip in New England

If you’d like to take some day trips from Boston, pin it for later.

4 thoughts on “35+ Amazing Day Trips From Boston Massachusetts”

Nice collection of day trips, but with the review of Salem, MA I can’t believe you left off both the Peabody Essex Museum (one of the best art and culture museums in New England) and no mention of any of the NPS sites and all the maritime history this city has.

I know the Peabody Essex Museum is amazing. I’ve written about it in my Salem article and in my article on the best museums in New England. I will add something here. But with a round up post, you can only write so much for each town.

This was definitely a trip down memory lane. I lived in New England for 23yrs and visited many of these destinations. You certainly did a great job on the history. I especially enjoyed the colorful pictures. I am drooling over just the thought of the lobster rolls on the Maine and New Hampshire coast.

I would love a lobster roll right now!

Leave a Comment Cancel reply

Save my name, email, and website in this browser for the next time I comment.

Last Updated on July 4, 2023 by Leslie Livingston

2 Days in Boston: The Ultimate Weekend in Boston Itinerary

We adore Boston, and I love writing detailed travel itineraries–so you’d think this 2 days in Boston itinerary would have been fairly easy to write, right?

As it turns out, a full summer of living in and exploring Boston in-depth with the intention of blogging about it resulted in having more favorite things to do in Boston than can be squeezed into a 2 day Boston itinerary–but lots of research and writing later, I managed to whittle down the best of Boston into a 48 hour Boston itinerary.

And, that surprisingly consequential summer led to another reason to return to Boston again and again: my Dad met my fabulous now-stepmom during that visit (hi, Christine!), and with 30 years of living in Boston under her belt, she has brought Boston and New England as a whole into our lives forever (and yes, she has provided many tidbits to help us enhance this Boston itinerary even further).

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

From someone who spent 3 months living there and fell head-over-heels for the city despite assuming that wouldn’t happen, here is everything we recommend you do–plus all the logistics you need to know–to pull off the perfect 2 days in Boston.

Delicious food, literary interests, American history, pretty neighborhoods, penguins, and more can all be covered with just 2 days in Boston–but fair warning, your feet might be a bit sore at the end!

Table of Contents

The Ultimate 2 Day Boston Itinerary

But what about walking the freedom trail, don’t want to walk consider a duck tour., where to stay in boston, the boston go card: worth the money, have more than 2 days in boston, ma, where to eat in boston, getting around during a weekend in boston, read more about visiting new england (and beyond).

Day 1 in Boston Itinerary : Back Bay, Beacon Hill, and Beyond

Start your morning in the boston public garden..

The Boston Public Garden is one of our favorite places in the city: quiet and beautiful, it’s a great place to relax, take a walk, and enjoy a bit of peace and (relative) quiet in the midst of the hustle and bustle of the city.

Be sure to check out the Make Way for Ducklings Statue, put in place for the famous children’s book that features Boston, while you’re there! If you’d like to enjoy views of the Boston Public Garden from the water, the swan paddle boats in the garden’s pond are famously inexpensive at $4.50/ride.

Head to Back Bay for brunch and beautiful houses.

Back Bay is one of Boston’s trendiest addresses: here is where you’ll find stunning mansions, high-end shopping, and the occasional burst of surprising quirkiness (like The Fairy Shop , which features oodles of Harry Potter memorabilia and makes my inner eleven-year-old quake with joy).

Here are a few of the best places to check out as you explore Back Bay on foot!

Commonwealth Avenue

Some of the most fashionable addresses in Boston can be found on Commonwealth Avenue!

S tretching into Back Bay from its endpoint at the Boston Public Garden, don’t miss the chance to walk down this stunning street and gawk at the beautiful homes.

This is a fantastic place to start your explorations of Back Bay.

Trinity Church

One of the most beautiful churches in Boston, this 19th-century church sticks out amongst the more modern feel of Back Bay.

Boston Public Library

In addition to being exquisitely beautiful, bibliophiles across the USA owe a debt of gratitude to the Boston Public Library for its continuing advances forward.

This was the first publicly funded library, the first library to open additional branches, the first to lend books out, and more recently, the first to install free wifi.

In other words, they’re pretty cool (and the reading room is a must-see during 2 days in Boston).

Peruse Brattle Bookshop.

As a book lover, I can’t write a 2 days in Boston itinerary without including the epic Brattle Bookshop !

Dating back to 1825 and specializing in used and rare books, Brattle Bookshop is located just off Boston Common and includes three stories and–my favorite–an outdoor courtyard stuffed to the brim with books.

Even if you don’t make it inside, the courtyard is worth seeing. I t boasts hundreds of inexpensive, used books (perfect for a cheap souvenir!) and enormous murals that climb the courtyard walls.

Stroll through Boston Common and enjoy views of the Massachusetts State House.

Boston Common is the heart and soul of Boston (and it’s definitely the Common, not the Commons, as locals will be quick to tell you).

W ithin a few minutes walk you can be in Beacon Hill, Back Bay, at the Massachusetts State House, at the theatre, shopping at Downtown Crossing (this is where you’ll find all the standard chain stores), or exploring a piece of American history.

The park is gorgeous to walk through, too. Be sure to stop by the carousel, take in the views of the gold-domed Massachusetts State House while you’re there , and count how many impeccably groomed golden retrievers you pass (it will be a lot) while you’re there!

Pay a visit to Beacon Hill.

Beacon Hill is my favorite neighborhood to explore in Boston.

This is the Boston you see on postcards: redbrick mansions, black shutters, a cobblestone path or two, tree-lined streets.

It is absolutely stunning to wander through–we recommend walking from Boston Common up to Louisburg Square, which boasts some of the most prestigious addresses in Boston (former Secretary of State John Kerry lives here), and then taking a quick stroll to Acorn Street to take advantage of one of Boston’s most photogenic spots.

Keep in mind that Acorn Street is very popular these days! Make sure to be respectful of people’s property (some residents have complained about visitors using their stoops–best to stick to the cobblestones).

Visit Park Street Church and Granary Burying Ground.

After enjoying a bit of time in Beacon Hill, head back down to Boston Common and pay a visit to the Park Street Church and Granary Burying Ground, which are right next door to the Common.

You’ll notice a large monument with a very familiar name in Granary Burying Ground: Benjamin Franklin’s parents are buried here, and a monument to the family is erected toward the center of the cemetery.

Stop by the King’s Chapel & Burying Ground.

The King’s Chapel is my favorite church in Boston to go inside–not because it is ornate, but because it is so unusual among US churches.

Built originally as an Anglican Church in the 18th century, the church has enclosed “boxes” instead of rows of pews.

Originally, prominent families who were members of the church would have a box of their own that they would sit in each Sunday.

The King’s Chapel still has an active congregation–but these days, instead of Anglicans, Unitarians call the chapel home.

Eat the original Boston Creme Pie at Omni Parker House.

Think you need to make a reservation and sit down to a meal to eat the original Boston Creme Pie?

You definitely don’t!

The Omni Parker House has a small shop on the first floor selling the delicious cakes, and we recommend stopping to pick one up.

If you want to also try the original Parker House rolls (which are, in fact, delicious), consider planning a meal–home to one of Boston’s many historic restaurants –at the Omni Parker House as well.

And, while we’ll talk more about hotels later, suffice it to say that if you’re looking for a luxurious, historic, and centrally-located place to stay in Boston, the Omni Parker House is a great choice .

Take a peek at the Old Corner Bookstore.

The former home of Anne Hutchinson has acted as a bookstore, apothecary, home, Boston Globe souvenir shop, diamond store, and now a Chipotle: talk about evolution!

The building is still worth a nod as you go by, though, and also happens to be set right across from the Irish Famine Memorial–a striking statue worth taking a look at during your 2 days in Boston.

Pay a visit to the Old State House and the site of the Boston Massacre.

As you wander your way through Boston on your way to the Old State House, be sure to note the Old South Meeting House along the way!

The Old State House and the site of the Boston Massacre that is right out front is the perfect final sightseeing stop on your first day in Boston.

As the oldest surviving public building in Boston, the Old State House has seen more than its fair share of American history: it was once the seat of the colonial government, then became the seat of the Massachusetts state government and eventually Boston City Hall.

The Old State House has been a museum since the 19th century, after more than 100 years in public service and a brief stint as a commercial building.

Day 2 in Boston Itinerary : Marketplace District, the North End, and the Waterfront

Begin in the marketplace district..

The marketplace district is all about the food, so come hungry and ready to explore as you start the second day of your Boston itinerary (just ignore the hideous city hall that’s across the street).

Here are the essential stops to make when visiting Boston’s marketplace district!

Boston Public Market

Looking for some New England specialties, whether to devour immediately or to take home?

Boston Public Market is the perfect spot for that: featuring exclusively New England-based products and companies, you can pick up anything from produce to donuts to crafts here.

This is one of my favorite spots in Boston–and not just because of how good the ice cream is!

If you’re lucky enough to have your 2 days in Boston overlap with a Friday or Saturday, be sure to swing by Haymarket (located right in front of the Boston Public Market) to check out a fabulous farmer’s market!

Faneuil Hall Marketplace

Made up of closely located Faneuil Hall, Quincy Market, South Market, and North Market, this is the heart of Boston’s historic market district–and also one of the most touristy places in the USA.

While we definitely feel it’s worth stopping by during your 2 days in Boston to appreciate the markets and the history behind them (Faneuil Hall dates back to the 18th century), unless crowds, chain stores, and overpriced food are your thing, you won’t need to stick around long.

Stop by the New England Holocaust Memorial.

Right in between the Boston Public Market/Haymarket area and the Faneuil Hall Marketplace sits the sobering New England Holocaust Memorial.

It takes very little time to walk through–no line, no entrance fee–but it is worth taking a moment to slow down and appreciate it.

Head into the North End.

Boston’s North End (also known as “Little Italy”, though you won’t catch a local calling it that) is the oldest neighborhood in Boston and a fascinating sort of place.

It’s one of the oldest parts of Boston, and is famous for being a neighborhood popular with Italian immigrants, though there are more tourists than Italians there these days.

It’s home to tons of Italian food (from the very good to the very bad), beautiful architecture, several noteworthy spots in American history, and a couple of very famous pastry shops.

Paul Revere House

The oldest remaining building in downtown Boston once belonged to none other than Paul Revere!

Whether you head inside for a tour or simply admire the facade as you walk by during your 2 days in Boston, be sure to note this piece of American history sitting in the North End.

Old North Church

And speaking of Paul Revere…

The whole “one if by land, two if by sea” story? That lantern was said to have been hung here, at the Old North Church.

(Modern note: there is a popular scam around the world that consists of fake monks collecting money–and they have a big presence right here. Best not to engage with them!).

Copp’s Hill Burying Ground and the Spite House

Boston’s second-oldest cemetery holds more than 1200 marked graves that include plenty of notable burials from the colonial era… but that’s not the only reason to visit.

Right across from Copp’s Hill Burying Ground sits the Spite House (also known as the Skinny House), which is home to one of my favorite Boston stories.

As the story goes, two brothers inherited land from their father. While one was away serving in the American Civil War, the other brother built a large home, taking over part of the soldier’s inheritance.

When the soldier returned home, he built the “Spite House”–incredibly skinny, and yet incredibly effective at blocking his brother’s view.

The legitimacy of the story is somewhat questionable, but it sure is a classic Boston tale.

Mike’s Pastry and/or Modern Pastry

If you’ve heard one thing about eating cannoli in the North End, it’s probably about how delicious Mike’s Pastry is.

If you’ve heard two things, it’s probably that Modern Pastry is better and more “unknown”.

Here’s what we can tell you firsthand: Modern Pastry is tasty, and the line at Mike’s Pastry was always too long for us to bother with (though we’ve heard from others it dies down sometimes–if you visit in the offseason, you might get lucky!).

And, if you are looking for a fantastic interior and an atmosphere that feels slightly like actually being in Italy, Caffé Vittoria is an even better option, though I’d have to do a back-to-back comparison to offer an opinion on the pastries (all of these places have tasty treats, though).

Regardless of where you choose to get one, we certainly recommend eating a cannoli or two during your 2 days in Boston.

Take a whale-watching cruise or visit the penguins at the New England Aquarium.

It doesn’t get more classic New England than a whale-watching cruise!

While the cruises require a bit of a time commitment (3-4 hours), if you’re hoping to hit the water during your weekend in Boston, a whale-watching cruise like this is an incredibly memorable option.

Of course, like all attractions involving animals in the wild, there’s no guarantee regarding how many whales you’ll see–but so many whales call Boston home that your odds are much better here than in many popular whale-watching ports around the world, to the point that many captains even guarantee at least one sighting during a trip.

Book your whale-watching cruise in Boston today!

Prefer to stay on dry land, or visiting Boston in the dead of winter when whale cruises aren’t available? If so, the New England Aquarium is one of the best aquariums we have ever been to.

T here’s a huge emphasis on conservation, the exhibits are striking and education-focused, and the aquarium’s location on the harbor means that it is even able to use the natural seawater for some of its exhibits!

Though the five-story ocean tank, complete with an ancient sea turtle named Myrtle, is incredible, the real showstopper for us is the penguins.

We adore penguins, and the New England Aquarium is home to several species.

If you want to see something truly adorable, visit the aquarium at 9:00 AM or 2:30 PM–aka penguin feeding time.

Want to avoid waiting? Purchase a  skip-the-line aquarium ticket  before you get there!

Take a stroll along the Harborwalk.

At around 43 miles long, you definitely won’t see even a quarter of the Harborwalk with only 2 days in Boston–but this continuous trail along Boston’s coastline is definitely worth checking out for a little bit.

Luckily, the New England Aquarium is located right on it, making it easy to go for a walk before or after your visit.

Enjoy the sunset from the water with a harbor cruise and/or dinner in the North End.

The perfect end to a 2 day Boston trip isn’t in Boston at all–it’s in the water, staring back at the city that boasts one of my favorite skylines in the world.

If you didn’t already take a whale-watching cruise, we recommend taking a harbor cruise around sunset to enjoy the end of the day.

C ruises are available at literally all price points, from a basic group cruise in a shared boat to a memorable cruise on a tall ship and beyond.

For a less expensive harbor cruise,  this sunset cruise  is a great option!

Had enough of the water for today–or want to enjoy a fabulous dinner after the boat ride?

If so, consider saying goodbye to Boston with a fabulous Italian-American dinner in the North End.

Like many iconic neighborhoods around the world, you’ll find a mix of mediocre-to-terrible tourist traps and delicious restaurants here, so it’s imperative to check reviews before sitting down!

We have loved our experiences at both  Ristorante Euno  and  Tresca  (pictured below: everything was delicious, but their house special of chicken parm made with vodka sauce was a standout!).

If you know one thing about what to do in Boston, it’s probably the Freedom Trail.

T he famous 2.5-mile trail covers 16 historical sights related to American history in Boston and is easily one of the most popular things to do in the city.

So don’t worry–it’s definitely on the list!

In fact, 14 of the 16 sights on the Freedom Trail are covered in this 2 days in Boston itinerary, including Boston Common, Park Street Church, King’s Chapel, Faneuil Hall, every historical sight I discuss in the North End, and more.

If you follow this itinerary during your weekend in Boston, you’ll spend quite a bit of time walking the Freedom Trail, and you’ll have tons of opportunities to check out the brick markings that denote where it leads!

Rather than simply list something so vague and malleable on our 2 days in Boston itinerary, though, we wanted to be sure to give specific suggestions.

A fter all, the trail can be seen in any order and doesn’t need to be done all at once .

Cheesy? Yes.

Entertaining? Absolutely.

Boston’s Duck Tours are famous for the unmistakable truck-slash-boat contraptions that they cart tourists around in by both land and sea.

Corniness aside, if you’re looking for an excellent way to get an overview of Boston’s most famous sights and history without too much walking, signing up for a Duck Tour might be the right choice for you!

The tours do sell out, especially in the summer, so be sure to book in advance if you want to make a Duck Tour part of your 2 days in Boston itinerary!

Book your Boston Duck Tour today!

With only 2 days in Boston, we recommend staying somewhere close to the T (aka Boston’s subway) that is near the center of the action.

The North End is a tempting option, but it is fairly difficult to get in and out of. Instead, we’d recommend staying somewhere in Back Bay or the Historic Downtown if possible. The Theatre District (near Downtown Crossing and Chinatown) is another solid option with a great central location.

If budget is an issue, you may need to go a bit further out. That’s not a problem–just make sure you’re within walking distance of a T stop!

For budget travelers not willing to sacrifice on location,  the HI Boston Hostel  is a great option.

Mid-range travelers will love the location (and breakfast) at  the Boston Park Plaza .

Want access to a kitchenette in your room?  Copley House  features some studios and apartments!

For travelers looking to splurge, the  Boston Omni Parker House Hotel  has it all: history, a prime location on the Freedom Trail, plenty of ambiance, and of course, the original Parker House rolls and Boston cream pie served right on-site.

Check rates & book your stay in Boston today!

The Boston Go Card is promoted as an all-access pass, allowing you to buy included and/or discounted tickets to dozens of Boston attractions at once.

With this 2 days in Boston itinerary, you won’t need it: the 2-day pass won’t allow you to break even or get ahead with the attractions we opted to include here (after all, so much of Boston is about exploring outside, on foot–which is free).

However, if you’re staying in Boston longer, or you are interested in participating in a Hop On/Hop Off trolley tour , completing a Fenway Park tour, visiting View Boston on top of the Prudential Tower (the new version of the old Skywalk Observatory), or visiting several museums, then the Boston Go Card is probably the right option for you.

Find out more about the Boston Go Card and see if it’s right for you!

Boston is full of things to do: even after 3 months in the city, plus return trips, we still have a list of unchecked Boston bucket list items longer than we would like.

If you’re lucky enough to have more than 2 days in Boston, consider visiting Revere Beach (it’s the oldest public beach in the USA!), touring the Samuel Adams Brewery, attending a Boston Red Sox game (or just touring Fenway Park, the oldest baseball stadium in the USA), taking a walk along the Charles River Esplanade, or heading out a bit farther along the Freedom Trail to take in the two remaining sights not covered on this itinerary, the USS Constitution and the Bunker Hill Memorial.

If you’re a museum fan, Boston has enough to keep you occupied for months: for example, the Isabella Stewart Gardner Museum is built in the form of a Venetian palace, holds gorgeous artwork, and is the victim of a heist .

For science lovers, the home of MIT and Harvard has you covered: the Boston Science Museum and MIT Museum are both worthy of a visit.

With time to plan in advance, consider going stargazing at the Coit Observatory.

If you’re visiting in the summer, a visit to the Harbor Islands is always a good idea for nature lovers .

Looking for day trip ideas? Salem, Rockport, Newport, Concord, and Lexington are all popular for good reason, and less-iconic but gorgeous New England beach towns like Hingham, Cohasset, and Hull offer less-crowded and more easily accessible day trip options than the Cape.

I could keep going forever, but suffice it to say: you can do a lot with only 2 days in Boston, but you can’t do it all!

We are far from experts on Boston cuisine, but we have had some truly stellar meals in Boston. .. and also asked my stepmom to help us round this section out a bit.

Here are some delicious restaurants that can easily fit into your 2 days in Boston itinerary!

Buttermilk & Bourbon — Commonwealth Avenue (Back Bay)

I love biscuits.

More than that, I love southern biscuits, and I’ve been eating them all my life, in North Carolina and beyond.

So when I say that Buttermilk & Bourbon serves southern-style biscuits so delicious that I still think of them fondly a year later, I really mean it.

All of the food we had was incredible, and we can’t recommend their brunch enough (and I assume lunch and dinner are fabulous as well).

Neptune Oyster — Salem Street #1 (North End)

I’m not a huge oyster fan, but Jeremy sure enjoyed these (and the lobster roll he happily consumed after downing the oysters).

A friend of ours took us here when she came to visit us in Boston, touting it as one of her favorite restaurants–and judging by the fact that she looked to be having almost a religious experience the entire time she was eating their oysters, it’s a well-earned spot on her list.

As the resident non-oyster eater, I can attest that their burger was delicious.

Ristorante Euno — Salem Street (North End)

Many Italian restaurants in the North End are duds.

Ristorante Euno is not one of them–in fact, this is the only restaurant in the USA we have eaten in that even begins to approximate having dinner in Italy.

We ate here with a big group and had the opportunity to taste everything from several kinds of pasta to veal to steak to we-stopped-counting-at-some-point amounts of wine, and it was all delicious.

Tresca — Hanover Street (North End)

I mentioned this restaurant above as well, but it’s worth repeating!

Offering a more modern twist on Italian food, Tresca draws inspiration from Tuscany in particular (though is solidly Italian American food, not traditional Italian).

The food, service, and ambiance were all excellent, and you can’t go wrong ordering the chicken parm with the house vodka sauce!

Tatte Bakery and Cafe — Charles Street (Beacon Hill)

Tatte Bakery & Cafe has several locations around Boston (and they’ve even expanded to the DC area since we first ate there), but the Beacon Hill location is easy to reach as part of your 2 days in Boston itinerary!

Home to delicious sweets, tasty sandwiches (I had a brie and prosciutto sandwich that was incredible), and pastries that look too beautiful to eat, Tatte Bakery is a great place for a snack or quick lunch while you’re running around trying to see Boston in 2 days.

Bell in Hand Tavern — Union Street (Marketplace District)

America’s oldest tavern has been pouring ale since 1795, so you’d assume that puts them at risk of being gimmicky with mediocre food, but nope!

We never had a bad dish at Bell in Hand Tavern, and their burgers are incredible.

If you’re hungry while in the marketplace district, this is the stop for you!

Union Oyster House — Union Street (Marketplace District)

Right across the street from America’s oldest tavern sits America’s oldest restaurant, which has been serving up seafood (and especially New England chowder) since 1826.

We didn’t eat here personally, and reviews are mixed–some say the food is excellent, some say it is just okay. Most agree that you’re paying a bit more to eat at a historical location, which is not surprising.

Regardless of the ups and downs, though, I couldn’t bear to leave it off–even if you just snap a photo of the exterior as you walk by on the Freedom Trail, it’s worth being aware of this landmark during your 2 days in Boston.

La Voile — Newbury Street (Back Bay)

Looking for delicious French food served in a beautiful setting?

If so, head to Back Bay to indulge at La Voile, where you can either order a la carte or opt for the nightly 3-course prix fixe menu.

You can enjoy your meal either indoors or outdoors, weather permitting, though you may want to make a reservation if you have a preference!

Parker’s Restaurant at Omni Parker House — School Street (Historic Downtown)

I’ll admit: the main dishes here were good-not-great for the prices they charge… but gorging ourselves on the original (and delicious) Parker House Rolls and Boston Cream Pie made us glad we experienced the food once.

If you want to try out Parker’s House, we recommend going for lunch or brunch to keep costs down a bit.

Dunkin’ Donuts — Literally Everywhere

… Or is that just “Dunkin'” now?

Okay, this is (mostly) on here as a joke–but okay donuts and subpar coffee aside, there’s no denying that grabbing a coffee at Dunkin’ is a true Boston cultural experience.

Boston is consistently rated as one of the most walkable cities in the USA and is also home to one of the densest public transportation networks in the country.

During our 3 months in Boston, we relied exclusively on the subway, the occasional bus, and our feet to get around the city, and we recommend you do the same during your 2 days in Boston.

There are two ways to buy tickets to the T, aka the subway/metro system: with a CharlieCard or CharlieTicket (which are free and reloadable), and individually.

The CharlieCards can be picked up from any attendant in the subway stations, but they aren’t always available.

While they can making paying for the T simpler, with only 2 days in Boston, I wouldn’t worry too much about getting one.

Bonus piece of history: if you ride the Green Line of Boston’s metro system, specifically between Park Street and Boylston, you’ll be riding on one of the oldest metros in the world (and arguably the oldest one in the USA).

Excited to hit the road soon and ready to keep planning your trip?

You can browse our 100+ blog posts about traveling in the USA here , or check out these guides:

• 55 Best Things to Do in Boston (+ Travel Tips!)
• 21+ Best Places to Visit in November in the USA (Fall Vacation Ideas!)
• 15 Wicked Fun Quotes About Boston
• USA Bucket List: 50 Best Places to Visit in the US
• 13 Epic East Coast Cities for Weekend Getaways

About Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

31 thoughts on “2 Days in Boston: The Ultimate Weekend in Boston Itinerary”

I’ve never been to Boston before but I would love to see Beacon Hill in person. It looks beautiful from the photos in your post. I also have a slight obsession with Boston Creme Pies so that’s a must try as well lol

Haha, yes, it definitely is! There are SO MANY amazing Boston Creme Pies in Boston… including in Beacon Hill! ;-)

Thank you so much for the time you spent in Boston so I could so easily enjoy the city on a quick stop. Your writing is engaging and your personal insights and recommendations so valuable. I have saved your site for future trips.

Thanks so much, Connie! We appreciate you reading. :-)

Hi! Great Itinerary! I’m heading to Boston this Friday for a week and I’m super excited to check out these places :)

Thanks so much, Evelyn!

Hope you have an amazing time during your trip to Boston! :-)

loved your page with all its information. I have a question : we are going to be staying at the North End soon at Battery Wharf , what is the fastest way to Salem ? I have heard there is a train from the North End straight to Salem. But I am really confused. Can you tell me your opinion ? I have copied your page and will use it for my trip. Thanks

Hi Kathy! Thanks for reading. :-)

Yes, a train runs from North Station (which is essentially right next door to the North End, it’s a quick walk away) directly to Salem. It’s a commuter rail, so very dependable and easy to use. We visited Salem that way personally and had no issues–it takes a little over half an hour to get there if I remember correctly.

Brilliantly written. Unfortunately not many of the pique my interest. Definitely worth the read and also learn a few things. Love it!

Thank you for this 2-day itinerary! We are looking forward to our time in Boston, and this will help us make the most of our short time there.

So glad we could help, Regina! Have a great time in Boston. :-)

Hi! Thanks for the info. Invaluable! Question. Can this be done easily on bikes or at least the harbor walk? Do you think we could fit in a Sam Adams tour in? What would you cut out?

So glad you found it helpful, Milissa! Yes, the Harborwalk is also a bike path, you can definitely ride there.

You can definitely rearrange things to fit a Sam Adams tour in! As for what to cut, it’s completely up to what you guys most prefer–I adored the penguins, for example, but some people wouldn’t care about the aquarium at all.

Some of the sites, such as Faneuil Hall or the Boston Common, can take anywhere from a few minutes to get a quick look at to an hour or more of perusing it in detail, so there’s a lot of flexibility with timing built in depending on your tastes.

Beacon hill is a tough pedal up, otherwise biking is fairly easy, although bike lanes are inconsistent.

I’d personally prioritize the uss constitution. It’s a free tour and think they are going below decks again as they weren’t for a while during covid.

Sam Adams is a good tour, but I might recommend harpoon instead. It’s closer, is almost as old, and is still local.

Hi, My husband & I will be in Boston in October for two days and I love this itinerary! Great job! So we’ll written! Thank you for sharing! One question… we will have a rental car and driving from Freeport, Maine. What is the best place to stay, B&B preferably, so that we can just walk from our B&B to all of these sites… and just leave our car at our B&B. Is that possible? We plan on driving to Plymouth and onto Rhode Island and then Connecticut after our time in Boston. Thank you for your help and suggestions, Pam

Thanks so much, Pam!

I’m not familiar with any BNBs off the top of my head that would meet both of those needs–generally, if you’re staying close enough into town to be within walking distance of the sights, small BNBs will have limited or no parking available.

I’d recommend plugging your requirements into your preferred hotel booking site (we use Booking dot com), including parking as a requirement, and seeing if anything pops up in a central neighborhood.

That being said, you can also park (paid, but convenient) in the garage under the Boston Common, which is very convenient for sightseeing!

Great post! Just what I was looking for. Real advice from a real person. Thanks for all of the great tips and restaurant suggestions.

Thanks so much, Andrea! Hope you guys love Boston as much as we do!

I love your post. Me and my husband will use your itinerary this weekend. Please give us suggestions of the hotels we can stay. We will be driving from Hanover NH and plan to park the car in the hotel, and we will just walk to all the places you mentioned for 2 days. Please let me know of your hotel suggestions. Thank you so much for your help.

Hi Susan! We have a few hotel recommendations in the post, after the itinerary section.:-)

Great review of my beloved city!!! But… I’m not sure how you could focus on Back Bay and not mention Newbury Street–filled with some of Boston’s best shopping and restaurants. Also, since I am a local, we would never refer to the T (formally known as the MBTA) as a metro. Honestly, if you said “metro” to any Bostonian, we wouldn’t know what you were talking about. Lol. Thank you for appreciating all the beauty Boston has to offer!!

Thanks so much, Patty! I hadn’t realized we didn’t mention Newbury Street in this post–it’s in our things to do in Boston post, though. :-) Beautiful street, I love it there!

Great 2 days itinerary!Really useful tips and informative content about boston.Thanks for sharing.

Hi Kate – loved the write up! We came to Boston in 2010 and fell in love with the town – and hence, have stayed on. If you ever edit the article – do please consider adding two great experiences: (1) that the Boston Library has one of the finest “afternoon tea” experiences in the world but has to be booked 4+ months in advance and 2) the nearby towns of Lexington (I live here) and Concord still have a ton of historical sites and ceremonies connected to the first revolutionary war… and are just 20-25 Min away at most from Boston Backbay.

I’ve had the Boston Library tea on my bucket list for years! One of my friends got to do it and raved about it. :-) Maybe next time!

This article and guide has been fabulous. My cousin and I are planning our first trip to Boston. It will be short, two and half days, prior to boarding a cruise ship. I cannot thank you enough for making it easy to map out, for the recommendations of places to eat and stay and for the history and photos. We want to make sure and hit all the highlights and to see the real Boston. This covers it all. Over the top great and I am so very thankful!!!

It makes my day to hear that, Sharon! Hope you and your cousin have a fantastic couple of days in Boston! :-)

Thank you for this post! My husband and I will be first-timers in Boston in October (14-18), and I was wondering if there are any fall specific activities/sights you’d recommend?

The main thing will simply be to appreciate the foliage, which you should definitely see! I’d plan to spend extra time in the parks, burying grounds, etc, as they’ll all be decked out in color.

If you have a chance to take a day trip outside of Boston, apple-picking (and apple-cider-donut eating) is a classic fall activity with plenty of options close to Boston. :-)

Salem is ridiculously crowded in October, of course, but it’s also an easy day trip from Boston, and arguably there’s no better time to visit than October! The whole town goes all-in on spooky season.

Thanks so much for this information! We will be traveling with my parents, and will have a couple of days in Boston. Mom gets around fine, but occasionally has trouble with her knees. Would you recommend a hop on/hop off bus or the duck tour instead of walking? I’m wondering about steep hills, and stairs – things of that nature. I am just asking for a general idea – I realize you have no way to assess someone’s abilities, lol! Your blog post will be a great help!

So glad you’ve found it helpful!

Much of the route is fairly flat, but Beacon Hill in particular has very steep sections–I’d be on the lookout for that.

A hop on/hop off tour might be a great compromise between going alone versus a fully scheduled option like a duck tour, as you can walk as much as makes sense but also always have another stop fairly close by. That way, you don’t have to commit to an enormous amount of walking at one time if energy starts to wane.

Leave a Comment Cancel reply

Search Site

5 Day Boston Itinerary

Boston, and the surrounding area, is full of pivotal historical sites, beautiful parks, delicious food and interesting museums.  Spending 5 days exploring Boston and the area around it will allow you enough time to try a bit of it all.  Here is our ‘5 Day Boston Itinerary’ perfect for seeing the best of Boston and the surrounding area. 

5 Day Boston Itinerary Overview

Day 1: walk the freedom trail, quincy market.

• Day 2: Lexington/Concord, Tour Harvard 
• Day 3: Day Trip to Portsmouth

Day 4: Boston Tea Party Museum, Boston Public Market, North End

• Day 5: Explore Salem 

Note: This itinerary is best set-up for arriving the day before and leaving the day after (this is what we did).  Alternatively, you could fly-in very early on day 1 and fly-out very late on day 5.  If traveling with littles, we do not advise this though.  Set yourself up for success and arrive the day before and leave the day after if you time allows. 

Disclosure: This article contains affiliate links. That means that, at no cost to you, we may get a small commission if you purchase through these links. This helps us keep providing travel resources for you!  

We took this trip when our daughter was 2.5 years old and our son was 8 months old.  For more information on exploring with a baby, please see our Top 10 Baby Travel Tips , How to Hike with a Baby , 5 Top Baby & Toddler Flying Tips and Flying with a Baby posts. 

On the first day of your 5 day Boston trip, walk the Freedom Trail.  This 2.5-mile trail takes you through the city to 16 different historical sites that were vital during the Revolutionary War and other historic events.  Walking this trail is a great way to see a lot of historical landmarks located in Boston in a relatively short time frame.  It’s also a great first day in Boston activity because it will help orient you to the downtown area.  On this trail you’ll see

• Boston Common (Boston Public Garden Adjacent to this)
• Massachusetts State House
• Park Street Church
• Granary Burying Ground
• King’s Chapel Burying Ground
• Benjamin Franklin statue and the former site of Boston Latin School
• Old Corner Bookstore
• Old South Meeting House
• Old State House
• Site of the Boston Massacre
• Faneuil Hall (Quincy Market across from here)
• Paul Revere House
• Old North Church
• Copp’s Hill Burying Ground
• USS Constitution
• Bunker Hill Monument

Be Your Own Guide

Download the Freedom Trail Brochure for more information on each spot on it.  We printed off this brochure and then took turns reading about the historical sites when we arrived at each while walking the trail.  You can alternatively take a guided tour of the Freedom Trail (offered by many different companies).  We opted for time independence, the ability to spend as little or much time at each spot as we wanted and the ability to deviate from the path as we desired.  We highly recommend this option as we spent a lot of time at Boston Common and then the adjacent Boston Public Garden (not part of the trail).  The Freedom Trail is easy to follow too.  Locate the brick path that marks the trail (2 bricks, sometimes painted) in the middle of the sidewalk (picture centered above of what the bricks look like) and simply follow it.  

We’d recommend budgeting at least 4 hours to walk this trail with breaks.  The most efficient way to walk it is to start on one end, walk to the other end and then Uber back to the beginning (if you need to get to your car).  We opted to start in the middle of the trail at Faneuil Hall/Quincy Market.  We first went southwest towards Boston Common, and then we retraced our steps back to Faneuil Hall/Quincy Market for lunch.  Then, we continued on the trail Northeast to the North End/Bunker Hill before retracing our steps back to Quincy Market.  It took us about 7 hours to walk the trail, but we walked it back and forth (started and ended at the same point) and took quite a bit of time to explore many spots just off but not on the Freedom Trail.  

Close to Freedom Trail Highlights

Some of our favorite stops while walking the Freedom Trail were not actually on the Freedom Trail but just off of it.  Hence why we think being your own tour guide of this trail, especially with how well the trail is marked, is your best option.  

Boston Common Park and Boston Public Garden

We spent a lot of time at Boston Common Park (part of trail) as well at the adjacent Boston Public Garden (not part of trail).  Boston Common Park is the oldest public park in the US.  It used to be a pasture for sheep and then a training ground during the Revolutionary War. Now it is a park where many famous people have spoken including Martin Luther Jr. and John Paul II.  It has a lot of open green space and paths.  There’s also a playground and a carousel at this park (not in operation during our visit though).  

Likewise, Boston Public Garden, across the street from Boston Common Park, was one our favorite places to explore in Boston.  This park is home to statues of the ducks from the Classic Robert McCloskey Make Way for Ducklings book.  Our daughter loved visiting these ducks SO much.  She ‘fed’ and hugged each.  She also had her stuffed cow ‘play’ with them.  The simple statues were such a hit.  At Boston Public Garden, there are also the iconic swan boats you can ride in the pond here (although not in operation during our spring weekday visit).  Further, if you are a fan of the show Cheers, you can hit up the Cheers Bar while here as it is right across the street from the park on the north side.  

Marlborough Street and Commonwealth Avenue

Some picturesque streets to explore, just east of the park, include Marlborough Street and Commonwealth Avenue.  These streets are lined with pretty townhouses and a tree-covered path even runs through the center of Commonwealth Avenue.  We actually visited these on another day (when we watched the Boston marathon) but easily could have added onto the Freedom trail.  These streets have all the northeast charm and are the perfect spot for a leisurely stroll.  If staying in the city center of Boston, we highly recommend being as close to these streets, Boston Common and Boston Public Garden as possible. 

Quincy Market 

About midway along the trail, the Quincy Market (not part of the trail), just adjacent to Faneuil Hall Marketplace (on the Freedom Trail), was another spot we enjoyed.  It is a good stop for a relatively quick and inexpensive bite to eat.  The market is filled with many different food vendors so everyone can get whatever type of food their heart desires.  We all opted for different specialty pizza slices from Regina Pizza , a Boston original pizzeria.  There was also an entertaining electric violinist in the main dining area and many other small specialty shops in the market.   As travelers who like people but not crowds, beware that this market is rather busy though. 

Greenway Carousel

Not far from Quincy Market is another one of our toddler’s favorite Boston spots, the Greenway Carousel .  This carousel is unique in that it is filled with animals native to the area.  It has whales, sea turtles, squirrels, rabbits, foxes and owls.  Our toddler got a real kick out of riding on both the fox and rabbit (and her stuffed cow got to ride too).  Each ride is only a couple dollars.   See our Boston with a Baby or Toddler post for more toddler and baby friendly Boston ideas.

Logistics Tip

If planning to drive into Boston and start/end your day at Quincy Market (like we did), you can park at the Boston Harbor Garage .  It is pricey ($44 a day) but very convenient and the price is on par with the other structures in the area.  If you arrive before 8:30 am though, parking will only cost you $25.  If you do not mind walking a little farther and are visiting on a weekend, park in this uncovered lot for only $5 (you will not find parking cheaper anywhere else in Boston, weekends only). 

Dinner at Paramount

If looking for a great dinner spot with super tasty food and tons of variety, head to Paramount in Beacon Hill . This restaurant has been open since 1937 and is well liked by locals and visitors.  As a party of 8, we each got something completely different but everyone liked it.  Even Natalie’s Dad, who may be the harshest critic, enjoyed it.  

Day 2 of 5 Day Boston Itinerary: Lexington/Concord, Tour Harvard 

On day 2 of your 5 day Boston itinerary, head to Lexington and Concord in the morning and then tour Harvard in the afternoon.  

Lexington is the spot where the Revolutionary war started on April 19, 1775.  On this day, Paul Revere rode from Boston to Lexington to warn the town that the British were coming.  The Revolutionary War then started here when the Redcoats arrived.   

The main historic attraction in Lexington to visit is the Lexington Green where the first clash between Minutemen and Redcoats happened.  Before walking around the Lexington Green, stop in the Lexington visitors center for a map that explains the Lexington Green sites.  We were able to walk the green at our own pace this way. Including our visit to the Visitors Center (fun souvenirs and some historic displays), we spent about an hour here.  There is also the Buckman Tavern Museum (where Minutemen prepared for the Redcoats arrival) you can tour.  Although we have not toured it ourselves, the general consensus from everyone we talked to is that the museum is not worth the cost of admission.  

Tip: Check to see if reenactment occurs during your visit.  We were visiting Boston around Patriots Day (April 19th, commemorates the start of the Revolutionary War) and there were several reenactments in the area.  Sam and Natalie’s Dad attended one at the Lexington Green.  It was a unique, and likely once in a lifetime, experience that any history buff would enjoy.  

Concord is only 5 minutes away from Lexington.  Like Lexington, it is another hub of key historical sites.  Here you can walk across North Bridge, the site of the Shot heard around the world, and watch the 30 minute “The Road to Revolution” presentation at the Minute Man Visitor Center.  If only doing these activities, budget an hour here.  If looking to spend more time in Concord, you can also walk 5-Mile Battle Road Trail that connects Meriam’s Corner in Concord to Lexington, visit The Old Manse (house that Ralph Waldo Emerson and Nathaniel Hawthorne both called home) and visit the Sleepy Hollow Cemetery (not “The Legends of Sleepy Hollow” Cemetery but where famous authors mentioned above are buried).  

In the afternoon on day 2 of your 5 day Boston trip, after visiting Lexington and Concord, head to Harvard for a guided tour of the first college founded in the US in 1636.  It’s very interesting to learn about this historic and prestigious college.  The college campus itself is beautiful as well with many historic brick buildings.  Harvard offers free guided tours daily.  We took the 3 PM tour.  Sign up the Friday prior online with the link above to the tour you want to take.  The tours do not book up instantly but be sure to set an alarm early in the morning on the preceding Friday to book the tour time you want to take to ensure you get the time/date you want. 

Day 3 of 5 Day Boston Itinerary: Day Trip to Portsmouth

On day 3 of your 5 day Boston itinerary, take a day trip to Portsmouth, New Hamshiphere.  Portsmouth is a charming New England port city about an hour north of Boston.  It is actually the 3rd oldest town in the US and is filled with colonial architecture.  Portsmouth’s downtown area has many local boutiques and restaurants.  Market Square, the center of this picturesque downtown, is easy to locate with the tall white steeple North Church as the focal point.  Start your visit to Portsmouth at Market Square as it is a good stepping off point for exploring the rest of the downtown area by foot. We spent the morning walking on brick lined streets and checking out the different local shops. 

Portsmouth Activities

Beyond the downtown area and local shops, this town has many other highlights including the parks, museums and waterfront eateries.  We enjoyed lunch at the River House .  Here we were able to dine on the waterfront and have some really delicious seafood (the best of our trip).  We then headed to waterfront Prescott Park .  This simple park has some walk out piers and some nice green space.  

Right next to this park is the open air Strawberry Bank Museum .  Although closed during our visit (open May-October), we were able to see some of the preserved historic buildings on the outside of the grounds.  Right across the street from some of the buildings of this museum is a park of swings (the highlight of our visit to Portsmouth for our toddler).  To round out our visit to Portsmouth, we drove across Memorial Bridge into Maine (we were able to be in 3 states in one day with only an hour of driving).  

Stop at a Local Ice Cream Stand

On your way back to Boston (set GPS to avoid tolls), be sure to stop at Lagos Ice Cream , a homemade ice cream stand with the BEST ice cream.  If you know us in real life, you know we take our ice cream very seriously and this ice cream was SO good.  There were about 50 flavors to choose from here. We tried the Funky Panda which is a vanilla based ice cream with caramel, oreos and coconut.  It was delicious and seriously the best ice cream we have had in a long time.  Important note–only cash is accepted.

On the 4th day of your 5 day Boston trip, head back into downtown Boston in the morning.  Today your first stop will be the  Boston Tea Party Ships and Museum .  At this museum, you’ll take a 75 minute tour of the Boston Tea Party ships and learn more about the history of the events leading up to and after the Boston Tea Party.  The actors that put on this tour really make it fun and engaging. You’ll even get to throw tea overboard into the harbor at one point.  This museum is open 7 days a week 10am-5pm (tours about every 30 mins) and costs $34/person.  You can make reservations in advance online but it seemed like there was plenty of availability on most tours to join as a same day/walk up add on. 

Parking Tip: If visiting on a weekend and driving into Boston, park in this uncovered lot for only $5 (you will not find parking cheaper anywhere else in Boston, weekends only). 

Boston Public Market for Lunch

After visiting the Boston Tea Party Museum, walk to the Boston Public Market for lunch.  This market is filled with local vendors and different food options.  Seafood, donuts, bagels, middle eastern food, etc.  This market was quieter and less bustling than Quincy Market, which was a welcomed change of pace. 

North End for Cannolis

After having lunch at the Boston Public Market, head to the North End for dessert.  The North End of Boston is the Italian district with all the best Italian restaurants and pastry shops.  Get a Cannoli from both Mike’s Pastry and Modern Pastry .  Many local Bostonians debate which shop has the better Cannoli.  Natalie votes Modern and Sam votes Mike’s.  Toddler votes both as “really good”.  You’ll have to try both to see which one you like better yourself! 

Day 5 of 5 Day Boston Itinerary : Explore Salem 

On the last day of this 5 day Boston Itinerary, head to Salem, the infamous site of the Salem Witch Trials in 1692.  This city is steeped in history and New England Charm as well.

Spend a ½ day or full day exploring this spooky city.   Start your time in Salem by stopping into the Salem Visitors Center .  Here, the staff will be able to tune in to any local happenings that day and give you a map.  From here, head to the Salem Witch Trials Memorial, about a block away north of the visitors center.  This simple memorial has stone benches for each victim of the witch trials.  During these trials, 19 people (14 women and 5 men) were killed.  Reading how each person died (most hung, one pressed to death) really drove home what happened here in the 17th century.  

Essex Street and McIntire District

After visiting the Salem Witch Trials Memorial , head north a couple blocks to stroll down Essex street.  This street is filled with many local and spooky themed stores.  Halloween really is a year round season here.  On Essex street, you’ll also be able to stroll past the Elizabeth Montgomery Bewitched Statue and the House of Seven Gables.  This house was made famous in Nathaniel Hawthorn’s book.  You can go inside of it but the consensus is that it is not worth the admission cost. 

From the House of Seven Gables, continue west on Essex street.  You’ll walk past the medieval appearing First Church in Salem and the historic Ropes Garden and Mason.  From here, head south on Chambridge street to Chestnut street.  Chestnut Street is part of the McIntire District in Salem.  This district is filled with some of the finest pre-twentieth century homes in America.  Many of Salem’s most important citizens, including Nathaniel Hawthrone, lived in homes here. Each house has a sign on it indicating the year it was originally built and any historical figures who lived there.  Walking up and down this street was our favorite part of our visit to Salem.  You can also head north and explore Federal Street to see more of these picturesque homes.  

Local Ice Cream, Coffee & Parks

After walking around Salem, head back downtown to get coffee and/or ice cream at two local shops, Odd Meter Coffee Co. and Melt Homemade Ice Cream ,  only one door apart from each other.  The homemade carrot cake ice cream at Melt was the perfect afternoon treat.  After this we headed to Salem Common Park where there was a nice playground for our toddler to play on.  If looking for a less bustling option to end your time in Salem, head to the lighthouse at Winter Island Park.  

We found Salem easy to navigate ourselves and appreciated being able to explore at our own pace.  If you’d prefer a guided tour, there are plenty of those too.  The visitors center will be able to tune you into any tours going on the day you visit.  

Where to Stay in Boston

On your 5 day Boston trip, we recommend staying in a central location a bit north of the city center.  A central location outside of the city will make day trips shorter and will be more cost effective than staying in downtown Boston.  We recommend staying at the High Rock Home in Lynn, about a 30 minute commute north of Boston. This condo’s central location, ample square footage, back patio, family friendly amenities and helpful host all made our stay great.  Read more on why we’d recommend this Airbnb in our Where to Stay in Boston as a Family post.   

We hope this guide helps you plan your 5 day Boston trip.  Anything you’d add to our guide? We’d love to hear your feedback and questions.  Please leave us a comment!

Did you find this post helpful? If so, please share it with a friend, like our Always Have a Trip Planned Facebook Page , follow our Always Have A Trip Planned Instagram and subscribe to our emails below.

And remember, Always Have A Trip Planned!

You may also like

10 day canadian rockies trip itinerary .

July 24, 2024

Top 3 Asheville Hikes

June 11, 2024

Asheville with a Baby or Toddler

Leave a reply cancel reply.

Your email address will not be published. Required fields are marked *

Save my name, email, and website in this browser for the next time I comment.

Sam Adams Brewery Tours

Top Things to Do

Free Things to Do

Things to Do With Kids

Skiing Near Boston

Beaches Near Boston

Hikes Near Boston

Boston Public Garden

Museums in Boston

Fenway Park Guide

Shopping in Boston

The Best Time to Visit Boston

Weather & Climate

Neighborhoods to Know

Driving in Boston

Public Transportation in Boston

One-Day Itinerary

Day Trips From Boston

The 13 Best Day Trips from Boston

Boston is a historic city with plenty of things to do and places to see, but there’s also lots more to explore outside the city limits. Whether you’re heading north to the mountains to ski or taking the ferry to Cape Cod’s Provincetown , there are day trips to take in every direction. Read on for our recommendations, all within driving distance and some you can even access by public transportation.

Portsmouth, New Hampshire

DenisTangeyJr/Getty Images

Portsmouth is a historic coastal New Hampshire city that may be small in size but is full of character and popular restaurants. Have drinks along the docks on Bow Street as the sun sets at Pocos , Martingale Wharf or the Old Ferry Landing . For a seafood dinner with a view, try Surf , also on Bow Street. And for a casual yet tasty breakfast, you can’t go wrong with Colby’s .

Those visiting Portsmouth will enjoy walking around Prescott Park and learning about the history of Portsmouth at the Strawbery Banke Museum . Make sure you reserve some time for walking around the downtown area and popping into shops along the way. This city is growing year-by-year, with hotels and condos being built up as it grows in popularity.

Getting There: Portsmouth is about an hour and a half from Boston and the best way to get there is by car. If you don’t have a car, you can also take the C&J Bus Line.

Travel Tip: Pack a beach chair and drive down Route 1A to take in the Seacoast’s beaches. One of the first destinations you’ll come across in Rye is Ordiorne State Park , where you can walk around along the ocean. Eventually, you’ll get to Hampton Beach before you cross back over into Massachusetts.

Boston Area Beaches

David Robinson/EyeEm/Getty Images

On a hot summer day, or even when the sun is shining in the spring or fall, there are plenty of beaches in the Boston area to spend a day relaxing at.

On your way back from Portsmouth, drive south along the ocean until you reach the beaches in Rye, or continue on to the popular Hampton Beach strip, where there’s a big beach and plenty of restaurants. Just over the Massachusetts border is Salisbury Beach, another day trip spot just over an hour north of Boston. Other beautiful beaches on Boston’s North Shore include Wingaersheek and Good Harbor Beaches in Gloucester , Plum Island Beach in Newburyport, Crane Beach in Ipswich, Singing Beach in Manchester-by-the-Sea and Revere Beach in Revere.

The South Shore’s beaches are equally as beautiful, with one of the closest options being Wollaston Beach in Quincy, and then many others including Duxbury Beach in Duxbury and Nantasket Beach in Hull. Of course, you can continue south to Cape Cod for plenty more beaches to choose from.

Getting There: Most of these beaches are only accessible by car and the furthest options listed are a maximum of 1.5 hours away, depending on traffic and where you are coming from. If you prefer public transportation , you can get to Singing Beach in Manchester-by-the-Sea and Revere Beach in Revere by the Commuter Rail and MBTA Blue Line, respectively.

Travel Tip: If you want to hit the beach but aren’t the type to stay from sunrise to sunset, try one of the beaches on New Hampshire’s Seacoast and then plan to stop explore Portsmouth before or after. The same applies to Plum Island and Newburyport. 

Newburyport, Massachusetts

ivanastar/Getty Images

Newburyport is another coastal town, which feels similar to downtown Portsmouth, New Hampshire in many ways. It was settled back in 1635 but has of course modernized over the years. Newburyport is most popular during the summer months given its location and nearby beaches, including Plum Island . But Newburyport is an ideal day trip from Boston at any time of year, as there are quite a few shops to stop by, restaurants to eat at and scenery to take in.

Getting There: Most people drive to Newburyport from Boston, as it’s under an hour and right off exit 56 on I-95 North. You can also take the Newburyport/Rockland Commuter Rail line from North Station.

Travel Tip: While you’re in Newburyport, drive over to Plum Island to spend some time at the beach, no matter what time of year. 

Provincetown, Massachusetts

Photography by Deb Snelson/Getty Images 

Located at the very tip of Cape Cod is Provincetown (also known as “P-Town”), best known as a gay resort community, but also a beautiful place to visit for a day, weekend or more. While driving to the end of the Cape may not seem like a day trip, it’s easy to get there via a 90-minute ferry through Bay State Cruise Company.

Provincetown is surrounded by water on three sides with several beaches to enjoy. Both during the day and in the evening, check out the downtown area’s restaurants, art galleries, boutiques and more.

If you're not able to make it to Provincetown, there are plenty of Cape Cod towns within a shorter driving range.

Getting There: Take the 90-minute Bay State Cruise Company ferry from Boston, which is the fastest way to get there. The ferry operates daily from mid-May to mid-October, with trips leaving Boston three times a day. If you prefer to drive through the Cape, it will take you over two hours, but typically longer, as the roads are oftentimes single-lane and traffic can be bad.

Travel Tip: You’ll find fresh lobster rolls all over Provincetown, but be sure to stop by The Canteen , which serves both hot and cold options.

Martha’s Vineyard and Nantucket, Massachusetts

grantreig/Gettyimages 

Martha’s Vineyard and Nantucket are two islands off the coast of Massachusetts, both of which are popular tourist destinations, especially during the summer months. Both are doable for day trips, especially Martha’s Vineyard, as it’s a bit shorter of a ferry ride. Both islands are quiet during the winter months, so plan your visit from Spring through Fall.

Vineyard Haven in Martha’s Vineyard, where the ferry drops you off, is full of shops and restaurants. You can also head to nearby Oak Bluffs, where you’ll find the 318 colorful Gingerbread Cottages at Wesleyan Grove off of Circuit Street. If you bring your bike or car along, you can explore the island’s beaches and other downtown areas as well.

Nantucket has different coastal vibe than Martha’s Vineyard and is also smaller in size. Here you’ll find cobblestone streets downtown and picture-worthy homes covered in hydrangeas all over the island. Of course, there are beautiful beaches around the island, along with food, galleries and boutiques. Stop by Cisco Brewers for a taste of local beer, which has become more and more popular throughout New England. And have a drink made with Nantucket’s Triple Eight Blueberry Vodka at one of the bars downtown.

Getting There: Martha’s Vineyard is a 45-minute ferry ride via the Steamship Authority from Woods Hole, which takes you to Vineyard Haven. The fast ferry to Nantucket is through Hy-Line Cruises , takes an hour and leaves from Hyannis. There are slower ferry options available, but these are the most efficient for a day trip. Keep in mind that Hyannis and Woods Hole are both on Cape Cod, so you’ll need to leave time for traffic if you’re traveling during peak hours. Both islands can also be accessed by plane from Boston’s Logan International Airport .

Travel Tip: You can choose to bring a car onto the ferry, but it’s recommended that you make plans for that in advance. That, coupled with the cost, is the reason many people choose to take a bike or get around Martha’s Vineyard through the Vineyard Transit Authority.

Providence, Rhode Island

About an hour drive south from Boston is the city of Providence, Rhode Island, also known as the “Creative Capital.” This city has become a popular tourist spot over the years, with popular attractions including WaterFire , a series of over 80 bonfires along downtown Providence’s three rivers, or the annual Halloween Jack-O-Lantern Spectacular or the Faces of the Rainforest exhibit at the Roger Williams Park Zoo . From November through March, head to the Providence Rink for Ice Bumper Cars .

Providence also has a foodie scene, with chefs coming from Rhode Island’s Johnson & Wales opening restaurants within the city, such as Oberlin , a seafood-focused small plates and tapas concept. If you’re looking for Italian, head to Federal Hill , the Little Italy of Providence. The Dorrance is another reputable spot, located within a former bank and serving globally-inspired New England cuisine. And while you’re in town, stop by PVDonuts for delicious and unique brioche donuts in fun flavors like fruit pebbles, butterscotch crunch and brown butter brownie.

Popular Providence hotels include The Dean , built around the city’s history and culture, and the Providence Biltmore , a historic property designed by the architects of New York’s Grand Central Terminal, and the Hotel Providence , another centrally located option that’s great for all types of travelers.

Getting There: Providence is an hour drive from Boston. You can also get there by train , including the Amtrak and MBTA Commuter Rail on the Providence-Stoughton line, both leaving from Boston’s South Station.

Travel Tip: For the best pizza in town, try no-frills Caserta Pizza , also known for their “Wimpy Skimpy,” a spinach pie stuffed with black olives, cheese & pepperoni.

Newport, Rhode Island

 Forty 1° North

Newport, Rhode Island is another coastal town within driving distance from Boston. Here you’ll find the makings of a perfect day trip, from the Gilded Age mansions and beaches, to walking along the famous Cliff Walk. Visitors also enjoy exploring the Brick Market Place , a downtown are with more than 25 shops and eateries. If anyone you’re traveling with is into cars, check out the Newport Car Museum , located in nearby Portsmouth.

Favorite Newport restaurants include The White Horse Tavern, America’s oldest tavern, Winner Winner , Scarpetta Newport , The Black Pearl and Mission Burger . If you plan on staying overnight, top-rated hotels and resorts include The Vanderbilt, Forty 1° North , Gurney’s Newport Resort & Marina and The Chanler at Cliff Walk . Many of these hotels

Getting There: Newport is an hour and a half drive from Boston and car is the easiest way to get there.

Travel Tip: Even if you’re not staying overnight, many of the top hotels are also great spots to grab drinks with a view if you’re in town for just the day. Head over to Forty 1° North and order your favorite cocktail as you look out on the water.

Nashoba Valley Winery & Other Vineyards

 Nashoba Valley Winery

New England may not have a full-blown wine country, but there are several family-owned vineyards that make for great day trips, with at least one option nearby no matter where you are staying. From Boston, your best bet is the Nashoba Valley Winery , where you can sample the vineyard’s wines and also pick your own peaches, nectarines and apples when they are in season and enjoy farm-to-table food at J’s Restaurant.

Another Massachusetts option is Furnace Brook Winery in the Berkshires, about 2.5 hours away from Boston. An hour north of the city, there’s South Hampton, New Hampshire’s Jewell Towne Vineyards. In Rhode Island, try Verde Vineyards or Carolyn’s Sakonnet Vineyard . As you head into Connecticut, follow the Connecticut Wine Trail and try the Lost Acres Vineyard in North Granby, Arrigoni Winery in Portland and Sharpe Hill Vineyard in Pomfret.

Getting There: The Nashoba Valley Winery is around an hour drive from Boston in Bolton, Massachusetts.

Travel Tip: If you plan on visiting several vineyards and wineries in one day, make sure you have a designated driver or look for transportation services, such as limos or tours to take you from one spot to another.

Mountains of Massachusetts and New Hampshire

JodiJacobson/Getty Images 

Speaking of Nashoba Valley, this destination is not only home to one of the best vineyards near Boston, but Nashoba Valley Ski Area is also a great winter destination for skiing and tubing if you’re into these activities but not long drives. Other places to ski in Massachusetts include Wachusett Mountain in Princeton, Blue Hills Ski Area in Canton and Ski Bradford in Haverhill.

As you head into New Hampshire , popular ski resorts and mountains include Waterville Valley Resort , Loon Mountain , Gunstock , Cannon and more. Another option, Bretton Woods , is not only a ski resort, but also home to the beautiful Omni Mount Washington Resort , which has plenty to do for both skiers and those who prefer après skiing activities. 

Getting There: Nashoba Valley Ski Area is less than an hour from Boston by car, and other Massachusetts ski destinations range between 40 minutes to a little over an hour. Most of the drivable New Hampshire mountains are just over two hours away from Boston.

Travel Tip: To make your ski trip even easier, try Liftopia Experiences , a service that will take you on trips from Boston such as skiing at Crotched Mountain or snow tubing at Ski Ward and to a local brewery. Outdoor retailer REI also offers classes and activities, such as a store to slopes shuttle  that takes you to Stratton Mountain.

Lincoln, New Hampshire

New Hampshire’s White Mountains is where you’ll find the town of Lincoln, where Loon Mountain is located. But that’s not all Lincoln has to offer. During the winter months, the Ice Castles are a picturesque destination to visit. You can also go ice skating at The Rink at RiverWalk Resort , which was transformed from a 167,000 gallon swimming pool that’s available for guests in the summer. While you’re at the RiverWalk Resort, take a sleigh ride, go snowmobiling or taste wine at the Seven Birches Winery , which is right on the property.

Getting There: Lincoln is about two hours from Boston without traffic and your best bet for getting there is by car.

Travel Tip: Beware of traveling north from Boston during the winter months on Friday afternoons and evenings, as it’s likely you’ll run into traffic leaving the city as locals get out of work and head to the mountains. 

Plymouth, Massachusetts

DenisTangneyJr/Getty Images

One of the best spas in the Boston area is located south of the city in Plymouth at the Mirbeau Inn & Spa . There’s more than just great massages and facials here – there’s a heated foot pool surrounded by lounge chairs to relax in, as well as an outdoor jacuzzi to enjoy while you sip champagne from the bar.

While you’re in Plymouth, take a walk along the water and check out the iconic Plymouth Rock and Pilgrim Hall Museum , America’s oldest, continuously operated, public museum filled with artifacts that came to our country with the Pilgrims. Then head 3 miles down the road to the Plimouth Plantation museum.

Nearby in Carver, the kids will enjoy the Edaville Family Theme Park , which is particularly fun around the holidays with their Christmas Festival of Lights. 

With Plymouth being on the water, there’s plenty of fresh seafood and outdoor dining, with restaurant favorites including Woods Seafood , Rye Tavern , East Bay Grille and Cabby Shack .

Getting There: The easiest way to get to Plymouth is via car, which will take about an hour. There is also a Commuter Rail stop in Plymouth if you prefer public transportation.

Travel Tip: While the Plymouth Rock is certainly a Massachusetts landmark, don’t be surprised when it’s nothing substantial when you see the remains in person. There is still plenty to see and do in Plymouth though!

Portland, Maine

DenisTangneyJr/Getty Images 

Portland, Maine may sound far away from Boston, but at two and a half hours away, it’s still doable for a day or weekend trip. This coastal downtown area has developed quite the foodie scene and it’s also a great spot to take in New England’s fall foliage season . Top restaurants include Fore Street , Central Provisions , Duckfat , Eventide Oyster Co. and Holy Donut . If you’re into beer, go for a tasting at Shipyard Brewing Company .

You can spend an entire weekend walking around downtown Portland and popping into shops, restaurants and bars. But another fun activity when the weather is nice to take the short ferry over to Peaks Island , where you can rent bikes or golf carts to cruise around the island and take in the coastal views.

Getting There: Portland is about two and a half hours away from Boston by car. Another option is to take Amtrak’s Downeaster from North Station in Boston to Portland, which takes about the same amount of time.

Travel Tip: Fore Street won a 2018 TripSavvy Editors’ Choice Award as one of the Best Iconic Restaurants & Fine Dining . This restaurant books up far in advance, but they reserve spots for walk-ins. The trick is to put your name in right when they open at 5:30 p.m.

Wrentham, Massachusetts

Wrentham Village Premium Outlets

Just south of the city are the  Wrentham Village Premium Outlets , a shopping plaza where both locals and tourists go to get lots of shopping done at once, especially around the holidays. As New England’s largest outdoor shopping center, you’ll find everything from Off Saks and Tory Burch, to Vineyard Vines and the Nike Factory Store.

Getting There: The Wrentham Village Premium Outlets are located just 35 miles south of Boston, right off exit 15 on I-495. The best way to get there is by car.

Travel Tip: Bring your AAA card if you have one. When you get there, show it at the visitor center to get a coupon book that will give you even more discounts than you get at the outlets. 

How Couples Can Have Fun in Boston

Boston Tea Party Ships & Museum: The Complete Guide

Best Romantic Hotels in Boston for Couples

The Complete Guide to Theater in Boston

How to See Boston in One Day

Little Kids Would Have a Ball at CoCo Key Boston Water Park

Sam Adams Brewery Tour in Boston

Boston's Black Heritage Trail: The Complete Guide

Getting Around Boston: MBTA "T" Subway System

Georges Island: The Complete Guide

Your Trip to Boston: The Complete Guide

Guide to St. Patrick's Day in Boston: Festivals, Events, Things to Do

Hotels Near Gillette Stadium

The 15 Best Things to Do in Boston's Seaport Neighborhood

Fenway Park: The Complete Guide

The Top 9 Things to Do in Beacon Hill

New England Wanderlust

Connecticut , Maine , Massachusetts , New Hampshire , New York , Rhode Island , Vermont  ·  March 30, 2022

34 Awesome Road Trips From Boston & Best Itineraries (2024)

Boston is an amazing starting point for adventures all over New England and the Northeast. With so many options to visit tons of nearby coastal towns, exciting cities and plenty of quaint, charming villages, there are endless possibilities for road trips from Boston. And since I’ve been road-tripping and traveling all over the Northeast for over 10 years now, I know all the destinations that are worth your time.

This list includes destinations that are all individually under 6 hours from Boston, and if you’re looking for road trip itineraries that combine destinations from this list, be sure to scroll to the end for suggested itineraries to make the most of your road trip!

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

🚙 Need to rent a car for your epic road trip? I’ve got you covered! Click here to check the best prices on Discover Cars!

Best Road Trips From Boston

For this list, I’ve broken down the destinations into four categories: Coastal, City, Charming Towns and Luxury Getaways. For each destination, I’ve also included the time it takes to get there from Boston, highlights of the best things to do, what to expect once there, and nearby things to do.

Coastal Road Trip Destinations From Boston

1. plymouth, ma.

Distance From Boston: 40-50 minutes

If you’re looking for a quick, easy getaway from city life in Boston, a little road trip to Plymouth is a fun way to do that. While the town is known for its history dating back to the early 1600s, they are also lots of outdoor activities, parks and beaches, and combine that with a small-town feel, Plymouth makes for a lovely little escape from Boston.

Best things to do in Plymouth:

• Plimoth Patuxet Museum is a living replica of the original pilgrim colony settlement. If you’re a history buff, this is a must-see. You can even climb aboard the Mayflower II, an exact replica of the ship that brought the pilgrims to Plymouth.
• Plymouth Long Beach is a 3-mile long stretch of public beach that’s perfect for getting out by the water.
• Plymouth Farmer’s Market is held every Thursday from May through October, and was Yankee Magazine editor’s pick for best Farmer’s Market in 2018.
• Brewster Gardens is a tranquil, waterfront park that’s sure to invite lots of relaxation.
• Walk around the charming downtown to visit the shops and restaurants,
• Pop into Dirty Water Distillery for an artisanal spirits tasting.
• Go on a whale watch tour with Captain John’s Boat Tours .
• Spend the day getting pampered at Mirbeau Resort & Spa , and even stay for lunch or dinner, or the night for the ultimate day of relaxation.

Click here to book your stay at Mirbeau Resort & Spa!

Psst! I have an entire post on visiting Plymouth, MA , if you need more ideas!

2. Cape Cod, MA

Distance From Boston: 1-2.5 hours, depending on where you to choose to go on Cape Cod.

With over 500 miles of shoreline to explore, Cape Cod is the ultimate beach road trip from Boston because you can get there in about 2 hours and feel like you’re in a whole other world. There are 15 towns in Cape Cod to choose from for your visit, and more beaches than anyone can count. Fill your days being ocean-side, exploring beautiful little coastal towns, eating fresh seafood and taking in amazing sunsets.

Best Things To Do on Cape Cod :

• Visit The Cape Cod National Seashore
• Explore Chatham’s downtown
• Visit Provincetown and the Pilgrim Monument
• For more on the best things to do on the Cape, click the link below for my detailed travel guide.

You may also enjoy:

• Can’t Miss Things To Do When Visiting Cape Cod For The First Time
• Best Things To Do On Cape Cod For Adults
• Best Towns To Stay In On Cape Cod
• What To Pack For Cape Cod
• Unique Things To Do On Cape Cod

3. Nantucket, MA

Distance From Boston: 2-3 hours, which includes time to park at the ferry terminal, and ride the ferry.

Nantucket is a gorgeous island off the coast of Cape Cod bursting with charm and natural beauty. A day trip to Nantucket is common while visiting Cape Cod, but staying overnight for a night or two would be the best way to make the most of your road trip from Boston. This is a great island to explore if you’re looking for stunning beaches and a beautiful downtown area.

To get to Nantucket, you’ll need to take the ferry from Hyannis on Cape Cod. From there, you can choose between Hyline Cruises or Steamship Authority to get to Nantucket.

Best Things To Do on Nantucket:

• Explore the shops and restaurants in the main town.
• Visit Brant Point Lighthouse.
• Rent a moped to explore the local beaches and towns.
• For more amazing things to do on Nantucket, click the link below for my detail travel guide on a Nantucket day trip.
• The Best Nantucket Day Trip Travel Guide
• How Many Days Do You Need On Nantucket + Suggested Itineraries
• How To Visit All The Nantucket Lighthouses

4. Martha’s Vineyard, MA

Martha’s Vineyard is the other island off the coast of Cape Cod, and it’s more popular as an overnight destination, versus a day trip because it’s bigger. Comprised of 6 beautiful towns, Martha’s Vineyard is home to beautiful beaches, quaint Main Streets for shopping and dramatic cliff-lined shores.

To get to Martha’s Vineyard, you’ll need to take a ferry from either Woods Hole or Hyannis (both terminals located on Cape Cod). There is no benefit to picking one over the other, and it’s best to just pick whichever location is more convenient for you (usually it’s Hyannis for most people).

Best Things To Do on Martha’s Vineyard:

• Gingerbread Cottages in Oak Bluffs
• Edgartown downtown and lighthouse
• Aquinnah Cliffs and Gay Head Lighthouse
• South/Katama Beach
• For more information on visiting Martha’s Vineyard, click the link below for my guide on deciding between Nantucket or Martha’s Vineyard for a day trip.

You may also find these Martha’s Vineyard posts helpful:

• Is Nantucket or Martha’s Vineyard Better For A Day Trip?
• The Ultimate Martha’s Vineyard Day Trip Guide
• How To See Martha’s Vineyard Without A Car

5. Marblehead, MA

Distance From Boston: 40-50 minutes.

Marblehead is an adorable little coastal town along the North Shore of Massachusetts, and a very quick road trip from Boston. This is the place to come if you’re looking for historical homes, small-town charm, great seafood, dramatic, rocky coastline and options for beaches.

Best Things To Do in Marblehead, MA:

• Marblehead Lighthouse & Chandler Hovey Park
• Self-guided historical home walking tour.
• Take in the views at Castle Hill Rock.
• For more information on the best things to do in Marblehead, click the link before for my detailed travel guide.

Click here to read even more awesome things to do in Marblehead!

6. Salem, MA

Distance From Boston: 30-40 minutes.

Salem is another little coastal town along the North Shore of Massachusetts, and is known for being the premier New England destination for all things spooky. While visiting Salem in October is definitely a bucket list-worthy goal, it’s actually a really wonderful town to visit all year round. It’s very walkable with a variety of things to do, and makes for a great day trip, or a weekend getaway.

Best Things To Do in Salem, MA:

• Winter Harbor Park and Lighthouse
• Salem Witch Trials Memorial
• Salem Maritimes National Historic Site
• Essex Street Pedestrian Mall
• House of Seven Gables
• Peabody Essex Museum

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

7. Rockport, MA

Distance From Boston: 50-60 minutes.

Rockport is one of my favorite coastal towns in all of New England. It has so much character, wonderful shops and restaurants, and really invites you to slow down a bit to take it all in. It’s a small town, and can be done in a day, but a weekend here would be a very relaxing road trip from Boston.

Best Things To Do in Rockport, MA:

• Visit Motif 1, the most painted building in New England, if not the country!
• Go for a scenic walk or hike at Halibut Point State Park.
• Meander through the shops on Bear Skin Neck.
• For more things to do in Rockport and the North Shore region, click the links below for my detailed travel guides.

Click here for more amazing things to do in Rockport!

Click here to read my travel guide on the best things to do on Cape Ann!

8. Newburyport, MA

Newburyport is a delightful little coastal town in Massachusetts that has a very traditional New England feel with beautiful homes at every turn, and an adorable little downtown area and waterfront park. Newburyport is also home to Plum Island, which is a gorgeous part of town with amazing beaches and wildlife sanctuaries.

Best Things To Do in Newburyport, MA:

• Visit Oldies Marketplace to look for antiques and treasures.
• Meander the streets of downtown to explore the beautiful storefronts.
• Take a leisurely stroll along the waterfront park.
• Pack a picnic or take a nature walk at Maudslay State Park , which has over 500 acres to explore.
• Head out on the open waters with Yankee Clipper Tours , and cruise around the Merrimack River and Newburyport Harbor.
• Drive over to Plum Island to visit Plums Island Beach, buy some handmade soaps at Plum Island Soap Co. , and walk the stunning nature trails at the Parker River National Wildlife Refugee .

Click here to read my full guide to visiting Newburyport & Plum Island!

9. Block Island, RI

Distance From Boston: 3-3.5 hours, which includes time to park at the ferry terminal, and ride the ferry.

Block Island is a beautiful island off the coast of Rhode Island with gorgeous beaches, walking trails, water activities, salt marshes, great restaurants and is overall a wonderful place to relax while appreciating the outdoors. This actually might be one of my top underdog suggestions for a weekend getaway from Boston.

It actually reminds me a bit of Prince Edward Island, so if you’re looking to live out your Anne of Green Gables dreams, but can’t make it to Canada, this is a great place to do that. There’s even a lovely hotel on the island called Avonlea.

To get to the island, you’ll need to drive to the Pt. Judith ferry terminal in Rhode Island. For more information on the ferry, click here .

Best Things To Do on Block Island, RI:

• Take in the views at Mohegan Bluffs.
• Rent a moped to explore the entire island.
• Spend some time swimming at Mansion Beach.
• Visit the island’s two lighthouses.
• Have lunch with a water view at The Oar .

Click here to read all my tips for taking a Block Island day trip!

10. Newport, RI

Distance From Boston: 1.5 hours, but always anticipate extra traffic crossing the Newport bridge.

Newport is a stunning coastal city in Rhode Island that’s the perfect destination for sailing, shopping, dining and being by the water. Even though it’s technically a city, I wanted to include it in the coastal destinations group because it definitely feels more like a resort waterfront town than a city.

With so many things to do, you could easily spend a weekend here, but Newport will also work for a day trip.

Best Things To Do in Newport, RI:

• Walk along Cliff Walk for amazing coastal views.
• Visit Bowen’s Wharf for shopping and dining.
• Grab a lobster roll at the Newport Lobster Shack .
• Walk over to Goat Island to see the lighthouse and take in views of the Newport Bridge.
• Sail around Narrangansett Bay with Sightsailing of Newport .
• Visit the unique shops along Thames Street.
• Grab lunch and cocktails at The Lawn at Castle Hill Inn , overlooking the water. Better yet, book an overnight stay for the ultimate Newport experience!

Click here to book your stay at The Castle Hill Inn in Newport .

Click here to read all my tips for taking a Newport, RI day trip!

Click here to read about all the best things to do in Newport, RI in the winter!

11. Mystic, CT

Distance From Boston: 1.5 hours

This adorable little town sits along Mystic River, and has an awesome mix of preserved maritimes history, small-town charm and nature. While Mystic is mostly visited for its quaint, waterfront downtown, it’s also home to parts of two bordering towns, Stonington and Groton, giving you opportunity to explore a few different coastal Connecticut destinations during your visit.

Best Things To Do in Mystic, CT:

• See penguins, beluga whales, sharks and sea lions at the Mystic Aquarium .
• Learn all about maritimes history at the Mystic Seaport Museum and Village , which is regarded as one of the best, if not the best, Maritimes museums in the country.
• Hit the trails at Bluff Point State Park.
• Take a sunset or moonlit cruise with Poet’s Lounge Sailing Charters .
• Grab a warm lobster roll, which originated in CT, at Ford’s Lobster in nearby Noank.

Click here to read about all the best things to do in Mystic, CT!

12. The Hamptons, NY

Distance From Boston: 5.5 hours if driving the whole way, 6 hours if you drive to New London, CT to take the ferry.

The Hamptons needs no introduction, as it’s become a famous summer destination in New York thanks to many celebrities calling it a secondary home. Sitting along the Long Island sound, you can expect gorgeous beaches, amazing shopping and restaurants, specialty food markets and farmer’s markets, wineries and plenty of opportunity for rest and relaxation.

The Best Things To Do in The Hamptons:

• Have a beach day and watch the surfers at Coopers Beach in Southampton.
• Go vineyard hopping, and taste some of the local wines. Channing Daughters Winery and Wölffer Estates are two great options.
• Take in the views at Montauk Lighthouse.
• Enjoy an afternoon of rest and restoration at the Montauk Salt Caves .
• Have some amazing and fresh seafood at Bostwick’s Chowder House in East Hampton.
• Rent a bike and ride along Gin Lane in Southampton for incredible views of the ocean, and to see some amazing houses.

13. Ogunquit, ME

Distance From Boston: 1 hour and 15 minutes

One of my favorite beach towns in all of New England is Ogunquit, which is one of the best places to visit in Maine in the summer , but it’s really fun in spring and fall, too. Offering both dramatic and rocky coastline that Maine is famous for, as well as a long, sandy beach that’s perfect for swimming, you’ll get the best of both worlds here. Ogunquit’s town is entirely walkable, so once you drive in, you’ll be able to leave your car behind and get almost everywhere by foot. There’s an amazing downtown scene with plenty of shops and restaurants, and you’re never that far from Ogunquit Beach.

Best Things To Do in Ogunquit, ME:

• Walk along Marginal Way, where you’ll get the most amazing views of the rocky coastline.
• Visit Perkins Cove to enjoy its charming shops and restaurants.
• Spend plenty of time at Ogunquit Beach, one of the best beaches in Maine.
• For more information on things to do in Ogunquit, click the link below for my detailed travel guide.

Click here to read about more amazing things to do in Ogunquit!

14. Kennebunkport, ME

Distance From Boston: 1 hour and 25 minutes

Just a short distance from Ogunquit is Kennebunkport, so these two destinations could easily be combined, and both are worth your time. Kennebunkport is full of character, and can be visited as either a day trip, or a weekend getaway, from Boston. Offering both beaches and a wonderful downtown scene, this is a great place to relax, unwind and enjoy being by the water.

Best Things To Do in Kennebunkport, ME:

• Visit Gooch’s Beach for a walk along the shore, or go for a swim.
• Have an authentic lobsterman experience with Rugosa Lobster Tours .
• Walk around the downtown and Dock Square shops.
• Grab an artisanal ice cream cone at Rococo Ice Cream .
• Have some craft cocktails and beer at Batson River Brewing and Distillery .
• Walk along Parson’s Way for amazing views of the dramatic coastline.
• Grab fresh seafood takeout from The Clam Shack .

Click here to see why Kennebunkport is one of the best Christmas towns in New England!

15. Bar Harbor/Acadia National Park

Distance From Boston: 4 hours and 45 minutes

One of the absolute best places to visit in all of Maine is Bar Harbor and Acadia National Park, and this will make an epic road trip from Boston. Bar Harbor is the adjacent town to Acadia, and where most people stay when visiting the park. Bar Harbor is a fun destination on its own because it’s full of character, and has great restaurants, and a beautiful harbor-side walking path and park.

Acadia National Park is one of the top destinations in all of New England, providing over 120 miles of hiking trails, and countless opportunities to take in some of the best and most incredible coastline views in the entire Northeast. In my opinion, this is one of the best roads trips from Boston you can take.

Best Things To Do in Bar Harbor & Acadia National Park:

• Walk along the Ocean Path trail inside Acadia, which is a flat, easy path along Shore Road that provides the most payoff for minimal effort when it comes to the most famous views in the park.
• Have lunch and popovers at Jordan Pond House inside Acadia, which offers views of the lawn and Jordan Pond.
• Drive to the summit of Cadillac Mountain inside Acadia for sunrise or sunset.
• Explore Bar Harbor’s downtown.
• Take a leisurely walk along Shore Path in Bar Harbor for the best views of the harbor.
• Visit Bass Harbor Lighthouse inside Acadia.

Tip : You’ll need to purchase a park pass to enter any attractions inside Acadia National Park. Park passes can be purchased online in advance by clicking here .

Psst! I have some posts on Acadia that you may find helpful, including my Acadia National Park Itinerary , and the Best Time To Visit Acadia National Park .

Luxury Road Trip Destinations From Boston

These destinations don’t have to be all about luxury, but since it’s nice to treat yourself every now and then, I wanted to include a few of my favorite luxury resorts that are easy road trips from Boston. If all you’re looking for is a little R&R and some serious pampering without having to leave the resort grounds, these are amazing places to visit.

16. Cliff House in Cape Neddick, ME

If you’re looking for the ultimate coastal Maine getaway to fully relax and recharge, then Cliff House will be the perfect road trip from Boston for you. This oceanfront resort sits atop 70 acres of cliffs, and offers incredible amenities that will allow you fully emerse yourself in Maine’s natural beauty without having to go far. Almost every square foot of this property has an ocean view, so there’s no way you can be stressed during your visit.

What To Expect During Your Stay At Cliff House:

• Beautifully-appointed rooms with a private terrace, and your choice of partial or full ocean views. Some rooms are also ocean-front.
• Complimentary coffee, tea and water stations on each floor.
• A full-service spa.
• Three oceanfront restaurants and a coffee cafe.
• Manicured gardens and pathways for relaxing walks.
• Two outdoor pools, two indoor pools and a hot tub.
• On-site shopping.

Click here to book your stay at Cliff House!

17. Ocean House in Westerly, RI

Distance From Boston: 1 hour and 45 minutes

For one of the very best luxury experiences in all of New England, Ocean House in Westerly, RI is a truly amazing destination. With the entire properly overlooking the Block Island Sound, it’s guaranteed you’ll be able to relax during your stay. Travel + Leisure has even named Ocean House as one of the top 100 hotels in the entire world.

What To Expect During Your Stay At Ocean House:

• Freshly designed and elegant coastal New England rooms and suites.
• Complimentary use of the hotels Mercedes-Benz convertibles for self-guided tours.
• Complimentary activities within the resort, such as daily yoga and cooking classes.
• Valet parking included in your room rate.
• Four on-site restaurants, and lobster dinners on the lawn during the summer.
• An on-site spa.
• Beautifully manicured lawns with yard games.
• Complimentary refreshments throughout the day.

Click here to book your stay at the Ocean House!

18. Mohonk Mountain House in New Paltz, NY

Distance From Boston: 3 hours and 45 minutes

If you’re looking for the ultimate road trip from Boston that combines hiking in the mountains with total relaxation, then Mohonk Mountain House is perfect for you. Located in the small college town of New Paltz, Mohonk Mountain House is right in the heart of the Hudson Valley of New York, and is surrounded by 40,000 acres of forest.

Overviews of the resort have been used in the Amazon Prime series Upload , and has long been rumored to be the inspiration behind Stephen King’s The Shining . But don’t let that scare you away! That only thing that will actually scare you once here is how amazing the views are.

If an overnight stay doesn’t work with your plans, guests can also purchase a day pass to the resort grounds, which allows you access to the hiking trails. This is a great way to enjoy the scenery without committing to an overnight stay.

What To Expect During Your Stay At Mohonk Mountain House:

• Traditionally-decorated rooms and suites that overlook the mountains. Most rooms also come with private balconies and rocking chairs.
• Lake Mohonk on the resort grounds.
• An all-inclusive stay where breakfast, lunch, afternoon tea and dinner, as well as all outdoor activities such as kayaks, row boats and canoes, are all included in the room rate.
• 85 miles of hiking trails right outside your door.
• Farm-to-table dining.
• Benches and chairs situated all over the resort grounds for moments of rest, and to clear your mind.

Click here to book your stay at Mohonk Mountain House!

Click here to read my detailed review of a Mohonk Mountain House Day Pass!

19. Mirbeau Spa in Rhinebeck, NY

Distance From Boston: 3 hours and 10 minutes

Mirbeau has a few locations throughout the Northeast, but my favorite of them all is in Rhinebeck, NY, a beautiful little town in the Hudson Valley. This particular Mirbeau Spa is one of the newer additions to their family, and is decorated in a modern, Parisian style, which makes it feel like a unique destination.

The spas at Mirbeau are really amazing. I’ve personally had massages and treatments at different locations, and they’ve always been consistent in quality (and, of course, relaxation). Guests are invited to walk around in robes, including at lunch, and the on-site hotel allows you to continue your relaxation journey into the evening for the perfect overnight stay.

What To Expect During Your Stay At Mirbeau in Rhinebeck, NY:

• A serene, calm spa atmosphere throughout the entire grounds.
• A relaxation room, aqua terrace and steam facility within the spa.
• Different spa packages to customize your stay that include dining options to make your visit stress-free.
• Luxurious and Parisian-inspired accommodations with options including in-room fireplaces and soaking tubs.

Click here to book your stay at Mirbeau in Rhinbeck!

Charming Small Town Road Trip Destinations From Boston

If you’re looking to visit some of the most charming towns in New England and New York for your road trip, I’ve got your covered! Here are the most adorable little towns to visit that make awesome road trips from Boston.

20. Saratoga Springs, NY

Distance From Boston: 3 hours and 15 minutes

While technically a city, Saratoga Springs’ historic downtown feels very much like a quaint village. Located in Upstate, NY and known for its horse racing track season, this destination has so much more to offer including a wonderful Main Street for shopping and dining, gorgeous parks, beautiful and historic architecture and live entertainment.

Best Things To Do in Saratoga Springs, NY:

• Walk around the grounds of Saratoga Spa State Park, which is a National Historic Landmark. You can enjoy a round of golf at an 18-hole championship course, have a picnic by the reflecting pool and admire the architecture of the Hall of Springs.
• July – Labor Day, visit the Race Track , and even try your hand at placing bets on the winner!
• Stroll through Congress Park, and find the mineral springs to taste the local water.
• Enjoy a healing bath at the Roosevelt Baths & Spa . The spa staff is trained on how to draw the perfect bath at just the right temperature, and the minerals in the waters have been said to have health benefits such as reducing sinus congestion and arthritis symptoms.
• Take in a live show at SPAC , one of the the country’s most renowned outdoor concert venues.
• Walk up and down Broadway, downtown’s main street, to visit the local shops and restaurants.
• Grab delicious cocktails with lunch or dinner at Morrissey’s Lounge & Bistro inside the famed Adelphi Hotel. Better yet, book an overnight stay at this Gilded Age-era boutique hotel, located in the heart of Saratoga’s downtown.

Click here to book your stay at the Adelphi Hotel in Saratoga Springs!

21. Skaneateles, NY

Distance From Boston: 5 hours and 20 minutes

Skaneateles is a lakeside town in the Finger Lakes region of Upstate, NY, and is a wonderful place to visit, especially in the Summer. With Skaneateles Lake right in the heart of downtown, and an adorable Main Street with really nice shops and restaurants, the quaintness of the town is perfect for rest and relaxation, but also offers plenty to do to keep from ever being bored.

Best Things To Do in Skaneateles, NY:

• Walk around Main Street to visit the boutiques.
• Sit and admire the views of the lake from the town’s many waterfront areas.
• Visit Anyela’s Vineyards to enjoy a tasting, or sip on a glass of wine and take in the peaceful views of the vineyards.
• Head out onto the lake for a boat tour.
• Grab dinner and drinks at the Sherwood Inn , located right in the heart of town, and just across the street from the lake.
• Spend the day getting pampered at Mirbeau Inn & Spa , the original Mirbeau location, which is home to a Monet-inspired garden and bridge.

Click here to book your stay at Mirbeau Inn & Spa in Skaneateles!

Click here to read more suggestions on the best things to do in Skaneateles, NY!

22. Lake Placid, NY

Distance From Boston: 5 hours

Known for hosting two Olympic games, Lake Placid in the Adirondack region of Upstate NY has so much more to offer (although, the Olympic sites are definitely worth visiting!). I personally love visiting Lake Placid in the winter because the alpine-inspired town really seems to come alive with apres-ski vibes, but it’s really a great destination all year round. While in Lake Placid, you’ll be surrounded by mountains and fresh air, and feel like you’ve truly escaped from every day life.

Best Things To Do in Lake Placid, NY:

• Walk around Mirror Lake, located in the heart of Lake Placid’s downtown.
• In the winter, enjoy skiing at Whiteface Mountain , and ice skating and a Toboggan Chute on Mirror Lake.
• Enjoy the miles of hiking trails in the nearby mountains.
• Walk around the alpine-inspired downtown village to visit the quaint shops.
• In the summer, go for a swim in Mirror Lake from the public beach area.
• Visit the Olympic sites, including the ski jump, ice arena and the Lake Placid Olympic Museum .
• Walk around High Falls Gorge, a 22-acre nature park with waterfalls.
• Grab drinks and lunch or dinner at The Cottage, a restaurant at Mirror Lake Inn Resort & Spa that sits right on Mirror Lake. Better yet, book an overnight stay, and also enjoy the on-site spa for the ultimate Lake Placid getaway!

Click here to book your stay at the Mirror Lake Inn Resort & Spa in Lake Placid .

Click here to read my post on all the best things to do in Lake Placid in the fall!

23. Hudson, NY

Distance From Boston: 2 hours and 45 minutes

Located in the Hudson Valley of New York, Hudson is known as being incredibly charming, and one of the best destinations for antiquing in the area. This is a great little town to visit if you’re looking to relax, enjoy a small-town atmosphere and see where the day takes you. Hudson is also a great destination if you’re looking to explore the entire Hudson Valley region.

Best Things To Do in Hudson, NY:

• Antiquing! There are countless antique shops in Hudson, and you’ll definitely want to check out The Antique Warehouse , which has over 300,000 sq. feet of treasures.
• Stroll down Warren Street, where most of the storefronts can be found.
• Take a boat cruise along the Hudson River with Hudson Cruises , which offers tours to the Hudson-Athens Lighthouse, and even murder mystery cruises!
• The Hudson Farmer’s Market is regarded as one of the best in the region, and is open every Saturday in-season, and also has a winter location February-April.
• Tour the local art galleries.
• Go for a nature walk in the Greenport Conservation Area, which is home to over 7 miles of trails, and is walkable from downtown Hudson.

Click here to read my post on the best things to do in Upstate New York in the fall!

24. Manchester, VT

This small little town in Southern Vermont is the perfect place to disconnect and relax. As you cross the New York/Vermont border, you’ll begin to see the tall mountains all around you, and instantly feel more at peace. In fact, you’ll be able to see the surrounding mountains from everywhere in downtown Manchester. And with everything to do from shopping and dining to hiking and nature walks, you’re sure to find something that everyone in your group will enjoy.

Best Things To Do in Manchester, VT:

• Hike or drive up Mt. Equinox, the tallest mountain in the Taconic Range, and enjoy the incredible views from above.
• Browse through Northshire Bookstore , an amazing independent bookstore that’s been in business since 1976. Here, you’ll find new and used books, a wonderful children’s section, and unique Vermont-inspired gifts and souvenirs.
• Visit Hildene , the Lincoln family estate, where visitors can tour the gardens, walking trails, farm land and indoor exhibits, and enjoy sweeping views of the Vermont countryside.
• Rent a tube at Vermont River Runners and take a relaxing water tube ride along the Battenkill River, which is perfect for a warm summer day.
• Grab a sandwich as big as your head at Zoey’s Deli . I also love their homemade chips!
• Hike the Lye Brook Falls trails to visit a beautiful waterfall. The trailhead is a short 5-minute drive from town center.
• Go for a dip in the Dorset Marble Quarry for a unique swimming experience!
• After your swim, visit the Dorset Union Store , a quintessential Vermont country store.

Click here for an awesome Vermont covered bridges tour itinerary!

25. Woodstock, VT

Distance From Boston: 2.5 hours

Of all the Vermont towns on this list, I think Woodstock might be my favorite. I love them all, but there’s something about Woodstock that just screams New England charm, and perfectly balances being a town that caters to tourists, while not losing any of the local character. It’s one of those idyllic towns you’ll daydream about moving to.

Best Things To Do in Woodstock, VT:

• Walk through the truly adorable village and enjoy the local shops and coffee cafes.
• Head over to the Woodstock Middle Covered Bridge, located right in the village, for a picture-perfect Vermont moment.
• Get your hands muddy with a pottery workshop at Farmhouse Pottery .
• Drive to nearby Quechee and visit the Simon Pearce Restaurant & Mill , and take in a live glass-blowing demonstration, as well as lunch overlooking the gorge.
• Head over to Quechee Gorge Village after Simon Pearce for some antiquing.
• Visit Billings Farm & Museum to tour a working dairy farm, gardens and orchards, and see live demonstrations. The grounds here are truly spectacular!
• Hike Mount Tom for stunning views of Woodstock from above.
• Best Places To Stay In Vermont In The Fall
• Best Things To Do In Woodstock, VT
• Best Winter Getaways In New England

26. Stowe, VT

Distance From Boston: 3 hours and 20 minutes

Stowe is an adorable little village in Northern Vermont that I love to visit, and it always puts a smile on my face. Even though it’s a well-known ski destination in the winter months, it’s a great little place to visit year-round will lots of outdoor activities and perfect Vermont scenery all over, including some beautiful covered bridges.

Best Things To Do in Stowe, VT:

• Hike Mount Mansfield, the highest mountain in Vermont, or drive the auto road to the summit.
• See if you believe in ghosts at Emily’s Covered Bridge. Legend says it’s haunted by a girl who hung herself on the bridge after her boyfriend never came to meet her.
• Walk the Stowe Recreation Path, a 5.5-mile long paved path that goes through beautiful scenery throughout the village. The path can be accessed from several locations in the village.
• Connect to the Quiet Path along the Rec Path, which is reserved for walkers only (meaning, no bikes wizzing by you). It meanders through parts of Mayo Farm, and is a very relaxing way to spend an afternoon.
• Go hiking at Smuggler’s Notch State Park.
• Visit the nearby Ben & Jerry’s Factory for a tour.
• Explore Sterling Falls Gorge.
• In the winter, hit the slopes at Stowe Mountain Ski Resort.
• Pick up some chocolates from Lake Champlain Chocolates.
• Best Things To Do In Stowe, VT
• Best Stops To Make When Driving From Boston to Stowe, VT
• Best Things To Do In Vermont In The Winter

27. Greenwich, CT

Distance From Boston: 3 hours

Greenwich is an absolutely beautiful town that sits right on the border of New York, and also very accessible to Manhattan. I love coming to this idyllic little town when I want a day of relaxing, shopping, dining, being outside, visiting the beach and enjoying the gorgeous scenery.

Best Things To Do in Greenwich, CT:

• Shop the stores along Greenwich Avenue.
• Enjoy a serene walk through the Donald M. Kendall Sculpture Gardens in nearby Purchase, NY.
• Meander through Montgomery Pinetum, a public park that’s very relaxing, and also has beautiful ponds, nature trails and gardens with an educational center and greenhouse.
• Head to the Lobster Bin for an amazing lobster roll on-the-go.
• Spend some time at the beaches along Greenwich Point Park.
• Admire the architecture of the historic district buildings.

28. Jackson, NH

Let’s head to the White Mountain National Forest in New Hampshire! One of the best towns to stay in is Jackson, where you’ll find a lovely downtown and Main Street, an iconic red covered bridge, and endless opportunities to explore the White Mountains region, including lots of hiking and outdoor activities. While it’s most popular during the winter for skiing, and the fall for foliage season, Jackson can be enjoyed year-round.

Best Things To Do in Jackson, NH:

• Visit Honeymoon Bridge, the town’s famous red covered bridge.
• Drive to the summit of Mount Washington, the highest peak in New England.
• Hike the Glen Ellis Falls Trail.
• Explore the downtown shops and restaurants.
• In the winter, go skiing at Black Mountain. In the summer, the mountain offers horseback riding and lots of hiking trails.

You may also like: The best things to do in New England in the fall!

City Life Road Trip Destinations From Boston

Even though you’re road-tripping from a city already, it’s still exciting to explore a new one. There are quite a few cities that make for amazing road trips from Boston, and many of them can be combined with other destinations from this list to offer the best of city life, and coastal or small-town living.

29. Portsmouth, NH

Distance From Boston: 1 hour

This charming little city is just a short drive from Boston, and definitely feels more like a town than a city. Portsmouth is a port-side city with a gorgeous downtown filled with quaint shops and boutiques, and is known as being a huge foodie destination. This is a great city to visit if you’re looking for a lot of character, and lots of options when it comes to being outside, dining and shopping.

Best Things To Do in Portsmouth, NH:

• Grab some fresh and delicious pastries from Elephantine Bakery , and be sure to enjoy them just outside the cafe in the most adorable little courtyard.
• Shop the boutiques in downtown Portsmouth.
• Walk along Prescott Park, which has over 10 acres of waterfront gardens and paths, and is home to live entertainment in the summer months.
• Take a dip in the water at Great Island Common Park.
• Go brewery hopping, as Portsmouth is home to five breweries.
• Enjoy a drink at the Book & Bar , a combined bookstore, cafe and bar.
• Head out onto the water with Portsmouth Harbor Cruises .
• Visit Portsmouth Harbor Lighthouse.

30. Providence, RI

Providence is the capital of Rhode Island, and also home to famed schools Brown University and the Rhode Island School of Design. It’s also a really fun city to be a tourist! With Providence River running through the city, you still have opportunities to feel like you’re connected to nature, and with tons of restaurants, shops, nightlife and history, this destination makes for an amazing road trip from Boston.

Best Things To Do in Providence, RI:

• Visit The Arcade , the country’s very first shopping mall designed with Greek revival architecture, and now home to some awesome boutiques and art galleries.
• Visit the Roger Williams Park Zoo , which is the third oldest zoo in the country, where guests can feed giraffes and other farm animals, and see over 160 different species while visiting. You can also jump on the Explore and Soar ride, which is a fun zip ride and train excursion through the forests.
• Enjoy a leisurely walk along the Providence Riverwalk.
• During the summer, experience WaterFire, where braziers are set with bonfires in the middle of the river.
• Take in the exhibits at the RISD Museum of Art.
• Take a Venetian gondola ride along the river at Waterplace Park.
• Do a self-guided historical walking tour along Benefit Street to see some of the city’s most historic houses and buildings.
• Take a boat tour along the Providence River.

Click here to read my post on the best day trips from Providence!

31. Portland, ME

Portland is an exciting waterfront city in Maine that sits on a peninsula along Casco Bay, and provides the best of both worlds as far as being a city destination that’s also coastal. With things to do outdoors along the dramatic coastline, to an amazing restaurant and food scene, Portland has a little something for everyone during your road trip from Boston.

Best Things To Do in Portland, ME:

• Portland Head Lighthouse is a must! It’s the most famous lighthouse in Maine, and one of the most iconic in all of New England. Nearby, you can also visit Spring Point Ledge Light and Bug Light, and do a mini lighthouse tour without leaving the city!
• Visit one of my favorite breweries in New England, Bissell Brothers . They also get bonus points for being close to the waterfront at Thompson’s Point.
• Meander around Old Port to see the city’s fishing industry come to life.
• Walk along the lively waterfront scene on Commercial Street for shopping, dining and water views.
• Tour the open waters on a beautiful Schooner tour with Portland Schooner . They also invite you to pack a picnic with beer and wine to enhance your experience.
• Tour the Portland Arts District, which is filled with art galleries, museums and theaters.
• Take a culinary tour of the city and learn the very best places to eat, led by a local. Click the link below to book your tour, or learn more info.

Click here to book your walking culinary tour in Portland!

You may also like:

• Best Boston Hotels Near The Aquarium
• Best Stops To Make Driving From Boston To Portland, Maine
• Best Day Trips From Portland, Maine
• Best Breweries In Portland, Maine
• Best Things To Do In New England For Your Bucket List

32. New York City

Distance From Boston: 3 hours and 45 minutes (but always allow extra time for traffic)

New York City needs no introduction, and if you’ve never been to the city that never sleeps, this is an absolute must if you’re looking into road trips from Boston. Below is a list of my absolute favorite things to do when I visit NYC, which includes the best things to do for first-time visitors.

The Best Things To Do in New York City:

• Walk the Brooklyn Bridge and visit DUMBO for sweeping views of both the Brooklyn and Manhattan bridges.
• Get bagels at Brooklyn Bagel (the best in the city).
• Visit Central park, and be sure to stop at Bow Bridge, Belvedere Castle and The Mall walkway.
• Grab a slice of pizza at Joe’s (150 E 14th St.)
• Explore the MET Museum and Cloisters.
• Take the Staten Island Ferry for views of the Statue of Liberty (this is free and way better than the official tours, which are super crowded!).
• See a broadway show.
• It’s touristy, but I love going to the top of the Empire State Building.
• Walk around the West Village for amazing streets and brownstones.

33. Burlington, VT

Burlington is a small and beautiful city in Northern Vermont that sits along Lake Champlain, and is wonderfully diverse, exuberant and also very relaxing. This is a great destination if you’re looking for a small-town feel set in a bigger city, waterfront and outdoor activities, an art scene and plenty of amazing restaurants.

Best Things To Do in Burlington, VT:

• Walk around Church Street, a pedestrian-only area lined with unique shops and restaurants.
• Stroll around the waterfront to admire the views of Lake Champlain, as well as the Burlington Breakwater Lighthouse.
• Bike the Burlington Bike Path, a beautiful path along the lake that’s over 7 miles long.
• Go kayaking or stand up paddleboarding on the lake.
• Head to nearby Shelburne to tour Shelburne Farms , one of my favorite things to do in all of Vermont! There are tons of hiking and walking trails through the 1400-acre picturesque grounds, and you can stop to sample their homemade cheeses and baked goods along the way.
• Take in the art scene on the South End, which is loaded with galleries and shops.
• Get a taste for the local brews with a Sip of Burlington Beer Tour. Join a small group for dinner, and learn from a local brew expert as you taste all the different beers that are brewed nearby. Click the link below to learn more, or book your tour.

Click here to book your Beer of Burlington experience!

34. Philadelphia, PA

Last but most definitely not least on our round-up of the best road trips from Boston, is the city of Brothery Love, Philadelphia. Philly is Pennsylvania’s largest city, and is deeply rooted in history, but there are all kinds of things to do from exciting nightlife and amazing food to parks and waterfront activities.

Best Things To Do in Philadelphia, PA:

• Run up the Rocky Steps at the Philadelphia Museum of Art, and snap a picture with the Rocky statue. A bit touristy, but if you’re a fan of the movie, you gotta go for it.
• Speaking of the Philadelphia Museum of Art , after your Rocky moment, be sure to visit. They have an amazing American art collection, as well as works by famed impressionists Renoir, Degas and Monet.
• Tour Independence Hall, regarded as the birthplace of the United States, and where the Declaration of Independence was debated by our Founding Fathers.
• Venture just outside the city to visit Longwood Gardens, an expansive garden oasis filled with both indoor and outdoor gardens and, and beautifully designed grounds.
• Grab a Philly cheesesteak at Woodrow’s Sandwich Shop .
• Stroll along the Delaware Riverfront to explore Cherry Street and Race Street Piers, and take in amazing views of the Benjamin Franklin Bridge.
• Hop on a BYOB trolley tour of the city, hosted by hilarious guides that share historic and entertaining information, and take you to some of the top sites in the city. Click the link below to learn more, or book your tour.

Click here to book your Historically Hilarious Trolley Tour in Philadelphia!

Road Trip Itinerary Options

If you’re looking to combine towns from this list into longer roads trips, or are wondering which towns are close enough to combine together to maximize your time and cover the most ground, I’ve got you covered! Below you’ll find suggested itineraries with different routes you can take while planning the best road trips from Boston.

Option 1: Massachusetts North Shore Road Trip From Boston

For this route, you’ll head north from Boston and visit the following destinations:

• Newburyport & Plum Island
• Portsmouth, NH

Days Needed For This Route: 2-4 . If you’re looking for an easy road trip from Boston with lots of options, this is an awesome route to take. You can do it in as little as 2 days for a weekend trip, or add on two additional days to take your time and explore each town.

Option 2: Cape Cod & The Islands Road Trip From Boston

For this route, you’ll head south from Boston and visit the following destinations:

• Martha’s Vineyard

Days Needed For This Route: 7-8 days. Because this route requires ferries from Cape Cod to the islands, and with Cape Cod being a larger region to explore, I recommend a week.

If you have less time, the islands could be done as day trips, and you could attempt this route in about 5 days . If you have 10 days, I would suggest spending one night in Plymouth, 5 days on Cape Cod, two nights on Nantucket and two nights on Martha’s Vineyard for the ultimate Cape Cod road trip.

Option 3: Boston To Bar Harbor Road Trip

This route will take you up the coast of Maine and stop in these destinations:

• Newburyport, MA
• Ogunquit, ME
• Kennebunkport, ME
• Portland, ME
• Bar Harbor, ME

Days Needed For This Route: 7-10 days. I suggest this much time because your final destination, Bar Harbor, is home to Acadia National Park, and there’s so much to see and do just in the park. And each stop along the way is a very worthy destination to spend at least one night in.

If you’re very short on time, you can do this route in 4 nights with this itinerary:

• On your way to Ogunquit, pass through Newburyport and spend 2-3 hours there. Arrive in Ogunquit late afternoon to spend the night.
• The next day, spend the morning in Ogunquit, and then drive to Kennebunkport to spend about 3 hours exploring there. Drive to Portland, and spend the night.
• The next day, spend your morning in Portland, and then drive to Bar Harbor to arrive by mid-afternoon. Spend 2 nights in Bar Harbor.
• Drive back to Boston.

I have a detailed Boston To Bar Harbor, Maine Road Trip Itinerary if you’d like more help with planning!

Option 4: Vermont Road Trip From Boston

For this route, you’ll head northwest of Boston, and drive through the best towns in Vermont from this list. You’ll cover these destinations:

• Manchester, VT
• Woodstock, VT
• Burlington, VT

Note : This route isn’t as direct as the other routes, and will include 6.5 hours of driving time to get from Boston to Burlington, stopping at the other destinations along the way. But then you can drive direct from Burlington to Boston on your way home, which will only take 3.5 hours.

Days Needed For This Route: 3-5 days . This could easily be a long weekend itinerary if you don’t stop in each town overnight, and just visit Manchester and Stowe for a few hours each. You could, of course, take your time, and do up to 5 nights for this itinerary.

Option 5: Rhode Island & Coastal Connecticut Road Trip From Boston

This route will take you southwest from Boston, and you’ll visit these destinations:

• Providence, RI
• Newport, RI
• Block Island, RI
• Westerly, RI

Days Needed For This Route: 3-6 days . This is another itinerary you could also do in a weekend if you only spend a few hours in Mystic, as a day trip from Newport, and skip going to Block Island. To visit all these destinations, you’ll need about 5 days, but 6 would be ideal to not feel rushed.

Tip : If you wanted to extend your road trip further along this route, there is a ferry that leaves from New London, CT, and goes to the Hamptons!

Option 6: Boston To New York City & The Hamptons Road Trip

This route will take you to these destinations:

• Rhinebeck, NY
• New Paltz, NY
• New York City
• The Hamptons
• Optional add-on: Philadelphia, PA

Note : The route from Boston to The Hamptons, while making all the stops in the Hudson Valley in-between, is not direct, and will take about 7.5 hours without stops, so I highly suggest you stop overnight in at least one of the towns to break up your drive. If you wanted to visit Philadelphia, this would be the route you would want to add that destination to, as you will have to drive through NYC to get there.

Days Needed For This Route: 1 week. To do this route in 7 days, I would suggest spending a few hours each in Hudson and Rhinebeck, then spend the night in New Paltz (splurging at Mohonk Mountain House is definitely worth it!). Then drive to NYC the next day, and spend 3 nights there. Then drive to The Hamptons, and spend 3 nights. If you want to add Philadelphia, you’ll want to add an extra night or two.

If you’re short on time and want to do this route in fewer days, I would suggest spending a night in the Hudson Valley (same as above), spend 3 nights in NYC, but include a day trip to The Hamptons. Or, if The Hamptons is of more interest to you, you could spend one night in NYC, and spend a night or two in The Hamptons. And then drive back to Boston.

The other option is to drive direct from Boston to New York City, and leave out the Hudson Valley towns entirely. On that route, your focus would be New York City and The Hamptons.

What Towns Are 1 Hour From Boston?

Plymouth, Salem, Rockport, Newburyport are all within an hour from Boston, and make for wonderful road trips or day trips from Boston.

Towns not mentioned on this list that are also an hour or less from Boston that are perfect for a road trip are Scituate, Gloucester, Manchester-By-The-Sea and Essex, all of which are located in Massachusetts.

What Cities Are 6 Hours From Boston?

New York City, Portsmouth, NH, Philadelphia, PA, Portland, ME, Burlington, VT and Providence, RI are all within 6 hours or less from Boston, and are all included on this list as amazing road trips from Boston.

Is Boston Close To Niagara Falls?

Boston is over 7 hours from Niagara Falls, and for that reason, didn’t make this list of road trips. But if you have extra time, it could be added to a road trip itinerary for Skaneateles, NY and the finger lakes region.

• 7-Day New England Road Trip Itinerary
• The Perfect New England Fall Road Trip
• Boston In The Fall: Fun Things To Do!
• The Best New England Gifts and Souvenirs to Look For During Your Trip
• 60+ Things To Do In Vermont
• Summer In New England: Best Places To Go & Things To Do!
• Incredible New England Resorts & Spas
• Best Time To Visit New England

That’s A Wrap On The Best Road Trips From Boston

As you can see, Boston is really an incredible gateway to all of the Northeast, making it easy to take lots of different road trips. Whether you want to explore the coast of Massachusetts and Maine, go cute-town-hopping through Vermont or visit as many cities as you can, you’re now ready to plan which of these road trips from Boston is perfect for you.

You might also enjoy

Subscribe To My Newsletter

• Privacy Policy
• Terms & Conditions
• Disclosure Policy

8 of the best day trips from Boston

May 23, 2023 • 6 min read

From the beaches of Cape Cod to the historic museums in Plymouth, here are the best day trips from Boston © Cavan Images / Julia Cumes / Getty Images

Boston is rich with historic sites, artistic venues, swanky restaurants and outdoor adventure, and if you want to keep exploring, there’s even more to discover in the areas surrounding the city.

Battle sites, beaches, colonial landmarks, creative outposts and of course seafood – plenty of seafood! – are all within striking distance of Boston and mostly accessible by train, boat, bicycle and bus.

From Salem to Cape Cod, here are the best day trips from Boston.

1. Take the ferry to Provincetown, Cape Cod

Travel time: 1 hour 30 minutes

At the outer tip of Cape Cod, Provincetown offers many delights for one little town – a collection of glorious beaches and bike trails through the dunes along the Cape Cod National Seashore , a vibrant artist community with galleries lined along Commercial St and a dynamic LGBTIQ+ scene. Another bonus: top-notch restaurants, such as Canteen , serving lobster rolls and crab paninis.

How to get to Provincetown from Boston: Provincetown is about 115 miles southeast of Boston. If you’re just coming for the day, the best way to get here is by ferry, operated by Boston Harbor Cruises (from Long Wharf) or Bay State Cruise Co (from the Seaport District).

2. Witness history at Minute Man National Historical Park

Travel time: 35 minutes

See where the Revolutionary War began on April 19, 1775, when colonial Minutemen stood up to the British Regulars who had marched out from Boston to confiscate their weapons. The two sides faced off first on the village green in Lexington (now called Battle Green ), and then near the North Bridge in Concord.

The National Historical Park includes the battle site at the North Bridge , as well as the route the soldiers followed (now called Battle Road ). Walking trails weave through the picturesque New England countryside past two informative visitor centers and a handful of historic buildings, where you can see ranger talks and musket demonstrations. Stop for a snack at Via Lago Café in Lexington or the Concord Cheese Shop in Concord.

How to get to Minute Man National Historical Park from Boston:  It's easiest to drive, but it's possible to take public transport. From South Station in Boston, MBTA commuter trains go to Concord. From the train depot, it’s 1.5 miles to the North Bridge Visitor Center, but you’ll need a vehicle to explore Battle Road. Ambitious travelers can cycle from Cambridge to Lexington on the Minuteman Commuter Bikeway (7 miles) and then continue to Concord via Battle Road (7 miles).

3. Remember the victims of the witch trials in Salem

Travel time: 1 hour

Salem has a rich but checkered history, from the colony’s tragic persecution of so-called witches in the 17th century to the town’s heyday as a maritime center in the 18th century. A score of sites recall the former, including a moving Witch Trials Memorial in honor of the victims.

Visitors can learn more about the area's rich sailing tradition at the Salem Maritime National Historic Site , which incorporates a handful of 18th-century buildings along Derby Wharf. Salem’s uncontested treasure is the Peabody Essex Museum , a wonderful collection of art and artifacts amassed from maritime trade. Stop at  Gulu-Gulu Cafe  when you need to recharge.

How to get to Salem from Boston: MBTA commuter trains run hourly from North Station to Salem. You can also take a pleasant ferry ride from Long Wharf, operated by Boston Harbor Cruises.

4. Learn about the Pilgrims in Plymouth

In 1620, a hardy band of Pilgrims set up the first permanent European settlement in New England at Plymouth. Visit the replica Mayflower II to imagine what their journey across the ocean might have been like. Afterward, head to  Plimoth Patuxet Museums  to experience what life in the settlement was like for the Pilgrims and the Native people who have lived there for more than 10,000 years.

Both sites are historically accurate "living" museums, with costumed actors portraying actual historical figures. You'll find plenty of places to stop for lunch along Plymouth’s main drag, such as  KKatie’s Burger Bar .

How to get to Plymouth from Boston:  MBTA commuter trains travel from South Station in Boston.

5. Admire the architecture in Providence

Providence , the capital of Rhode Island , is like Boston’s smaller sibling, with attractive walkable neighborhoods, elegant 18th-century architecture , dynamic and artsy student populations , and its own leafy Ivy League campus .

There's a lot going on here food-wise as well, some of it due to the presence of a world-class culinary school (Johnson & Wale), which means there’s a good meal just around the corner. Try Julian’s for lunch or brunch. On summer nights, the riverside Waterplace Park comes alive with street performers, art vendors, food trucks and dancing flames at  WaterFire , a non-profit arts organization.

How to get to Providence from Boston: MBTA commuter trains run from South Station to Providence. Amtrak trains are more expensive and slightly quicker.

6. Head to Cape Ann for seafood, beaches and whale watching

Travel time: 1 hour by car, 2 hours 30 minutes by public transportation

Welcome to "the other Cape," located along the North Shore of Massachusetts. The heart and soul of Cape Ann is Gloucester, a gritty fishing town with a thriving art colony at Rocky Neck and whale-watching cruises out to Stellwagen Bank .

Gloucester’s quaint, touristy counterpart is Rockport, with Motif No 1 on full display and souvenir shops lined up along Bearskin Neck. The rest of Cape Ann is a patchwork of beautiful coastal beaches and interior walking trails. Get your seafood fix at Causeway Restaurant in Gloucester or Roy Moore Lobster Co in Rockport.

How to get to Cape Ann from Boston: The MBTA commuter rail runs from North Station to both Gloucester and Rockport. The Cape Ann Transportation Authority operates five bus routes to beaches and villages around Cape Ann.

7. Swim, hike and explore at Boston Harbor Islands

Travel time: 50 minutes

Some 34 islands are scattered about Boston Harbor, comprising a unique state park that’s an easy jaunt from the city. Take your pick from Georges Island , site of Civil War-era Fort Warren, or Spectacle Island , with a supervised swimming beach and a rewarding lookout.

You can go farther afield to more remote islands that offer trail walking, bird-watching, fishing and swimming. Both Georges and Spectacle have good snack shacks, but there is no food or water on the outer islands. Packing a picnic is recommended.

How to get to Boston Harbor Islands from Boston: Boston Harbor Cruises offers seasonal ferry service from Long Wharf to Georges and Spectacle Islands, where another boat service runs to the outer islands.

8. Escape commercialism at Martha's Vineyard

Travel time: 2 hours 15 minutes

Bathed in unique beauty, Martha's Vineyard attracts wide-eyed day-trippers, celebrity second-home owners and urbanites seeking a restful getaway. The 15,000 year-round residents include many artists, musicians and back-to-nature types.

Just 7 miles off the coast of Cape Cod, Martha's Vineyard remains untouched by the kind of rampant commercialism found on the mainland – there's not a single chain restaurant or cookie-cutter motel in sight. Instead you'll find cozy inns, chef-driven restaurants and a bounty of green farms and grand beaches. Enjoy fine dining in gentrified Edgartown or hit the cotton candy and carousel scene in Oak Bluffs.

How to get to Martha's Vineyard from Boston: It's about a 90-minute drive from Boston to Woods Hole. From there, the car ferry to Martha's Vineyard takes around 45 minutes.

This article was first published Aug 21, 2019 and updated May 23, 2023.

Explore related stories

Destination Practicalities

Jul 16, 2024 • 8 min read

From gleaming storefronts and bars to historical sites and districts packed with international culture, these are Boston's best neighborhoods.

Jul 3, 2024 • 13 min read

Jun 21, 2024 • 5 min read

Jun 5, 2024 • 10 min read

May 9, 2024 • 9 min read

May 3, 2024 • 12 min read

Apr 29, 2024 • 11 min read

Apr 19, 2024 • 10 min read

Mar 26, 2024 • 6 min read

Mar 1, 2024 • 6 min read

• Meet the Team
• Our Manifesto
• Work with Us
• Budget Travel
• Personal Development
• Work & Travel
• United Kingdom
• More of Europe
• Philippines
• More of Southeast Asia
• More of South America
• More of Central America
• South Korea
• More of Asia
• More of North America
• New Zealand
• Pacific Islands
• More of Oceania
• South Africa
• More of Africa
• More of the Middle East
• Travel Essentials
• Travel Gear

Home » North America » Boston

BOSTON Itinerary • MUST READ! (2024)

Boston is the capital of, and largest city, in the state of Massachusetts. Boston was founded all the way back in 1633 making it one of the oldest cities in the United States, and it played a very crucial role in the American Revolution. You can learn all about its fascinating and important history during your weekend in Boston.

Planning a trip to Boston has never been this easy! The thriving port city has a myriad of exciting activities to take part in, as well as a multitude of sightseeing attractions.

If you’re up for the hustle and bustle of city living, with the peace and tranquility that comes with staying by the seashore, then a Boston visit is on the cards!

Here’s everything you need to know, to create your very own Boston itinerary!

Unlock Our GREATEST Travel Secrets!

Sign up for our newsletter and get the best travel tips delivered right to your inbox.

Best Time To Visit Boston

Where to stay in boston, boston itinerary, day 1 itinerary in boston, day 2 itinerary in boston, day 3 and beyond, staying safe in boston, day trips from boston, faq on boston itinerary.

If you’re wondering when to visit Boston , the answer is: there’s no time like the present! But there are certain weather patterns at different times of year that might suit your schedule best.

The most popular time to travel to Boston is between June and October. The weather is warm and there are plenty of outdoor festivals, football games and other exciting entertainment options to take part in!

The Broke Backpacker is supported by you . Clicking through our links may earn us a small affiliate commission, and that's what allows us to keep producing free content 🙂 Learn more .

From November to February Boston gets very cold, but if you can stomach it you’ll have plenty to celebrate! You’ll get the chance to enjoy reduced prices of accommodation, tours, and activities around the city, which is a major plus if you’re on a budget! Just remember to pack warm clothes as you’re sure to need them this time of year.

Between March and May is Boston’s springtime. The weather starts to warm (ever so slightly), but you can still enjoy discounted rates and peace and quiet at the many Boston attractions. If you’re a little wary of the weather, just take a few Boston walking tours as they’re sure to get your heart pumping in no time!

Save more and experience more. Get a city pass before you travel.

Looking for accommodation can be a tough job, so we’re going to make your life a little easier by telling you about the best place to stay in Boston !

South Boston is a great place to stay, especially if you’re a first time visitor to this wonderful city. The neighborhood hugs the bay and is home to the scenic waterfront! The waterfront is a stretch of land about 1-mile long, where Bostonians walk their dogs or go for romantic strolls in the evening.

In recent years, the neighborhood has experienced an influx of young professionals, so expect the days to be quiet and the evenings to be abuzz with activity and youthful cheer!

Jamaica Plain is a very diverse neighborhood, where everyone who aspires to be different tends to stay. You’ll find hipsters of every variety staying in this old and quaint neighborhood! Jamaica Plain is home to Jamaica pond, which is a large urban park, perfect for those looking to get out of the hotel for a jog or even a leisurely stroll.

Davis Square could be considered one of the most happening neighborhoods in town. The neighborhood is home to a lively mix of students, young professionals, and old-timers who still like to party! You’ll find a multitude of restaurants and cafes, bustling with a community of thriving individuals.

Need to know to where the best hostels in Boston are? Here are our top accommodation picks for your Boston trip itinerary!

Best Hostel in Boston – HI Boston

HI Boston offers an incredible communal setting that leaves you feeling refreshed to start touring Boston every morning! After indulging in a free breakfast at the hostel, be sure to play pool and engage with your fellow travelers. With a great central location, there’s no better hostel to add to your Boston itinerary!

Best Airbnb in Boston – Studio in Prime Location

Spack dab in the heart of Back bay is this astonishing home that offers one of the most comfortable stays in the city. It’s definitely one of the best Airbnbs in Boston . Located on the lively street of Newberry, you have access to the most premier shopping in the city and the award-winning restaurants you’ve only seen on tv. Speaking of food, the kitchen is small but does have everything you need to cook a quick meal, but being in the popping neighborhood, you will most likely be enjoying all the cafes he neighborhood has to offer anyways.

Best Budget Hotel in Boston – YOTEL Boston

This wonderful hotel is located in Boston waterfront and offers a rooftop terrace with panoramic views of the city! Guests can indulge themselves at the on-site restaurant that serves absolutely delectable dishes. Make sure you make use of the on-site fitness center and take a visit to the many nearby Boston attractions!

Best Luxury Hotel in Boston – The Eliot Suite Hotel

This historic hotel is located in Bostons’ iconic Back Bay area. The Eliot Suite Hotel is elegant and offers many perks, such as the on-site sashimi bar! Guests can also enjoy free access to the sports club and business center that provides a constant flow of entertainment for visitors to the hotel.

There are a hell of a lot of things to do in Boston . In order execute your Boston itinerary, you’re going to need to know how to get around!

When traveling through a few neighborhoods, taking the commuter rail is a great option! It travels around the outskirts of the suburbs, giving you access to a few different areas. It’s also a fairly cheap option, and possibly the best way to tour Boston.

Taking the bus is a very common way to get around the city. It’s perfect for intercity travel and is always decently priced. There are also extensive late-night routes for those still out and about in the early hours.

BlueBikes is a bicycle sharing system with over 100 stations and over 1000 bicycles throughout the city. If you’re looking for an easy way to get around while staying active, this may be the way to go. You can purchase a 24-hour card that gives you access to bikes all around the city for a day.

Of course, taking a taxi around the city is always an option, although traffic does tend to be an issue in rush hour, so be careful of the times you choose to take this form of transport. Taxis are also more expensive than other forms of transport, so we wouldn’t recommend it if you’re on a budget.

Want to save money on accommodation?

We got you. For reals.

Boston Public Garden | Boston Pond | Isabella Stewart Gardner Museum | Trinity Church | Little Italy

If you’re only spending one day in Boston, it’s important to hit some of the most popular tourist attractions in Boston . You’ll spend the day strolling through the Boston Gardens and taking a ride in the famous swan boats, before checking out an art museum, Trinity Church and finally exploring Little Italy!

Day 1 / Stop 1 – Stroll Through the Boston Public Garden

• Why it’s awesome: A large garden located in the heart of Boston, which is also the perfect place for a morning stroll.
• Cost: Free!
• Food nearby: The Friendly Toast Restaurant is a local favorite for those looking for early morning breakfast! After a stroll in the gardens you’re sure to have worked up an appetite, so be sure to try their delicious French toast or their incredible gluten-free pancakes!

Boston Public Garden is the oldest public garden in America, giving it a very old-timey feel. A Victorian bridge crosses the pond, and intricate statues are scattered around the lawns.

There is a series of paths that wind their way through the lawns, providing visitors with a wonderful view of the English-style garden. There is a formal garden area that was planted by the city in an attempt to make the garden even more appealing than it already is. The flowers planted blossom throughout the year to create a beautiful show.

The pond that acts as the centerpiece for the public gardens is home to a great number of ducks in the warmer seasons, as well as a few swans. There are even swan boats that have become a very popular tourist attraction in Boston during the summer.

While going for your morning stroll in the public gardens, be sure to look out for the Equestrian statue of George Washington, which is a very interesting piece that seems to have gained popularity over the years.

Day 1 / Stop 2 – Ride on the Pond

• Why it’s awesome: There are many ways to enjoy the pond, depending on what time of year you decide to visit Boston.
• Cost: Adults USD $4 and Children USD $2.50
• Food nearby: Saltie Girl is a highly unique restaurant that has become a favorite amongst the locals. They serve incredibly fresh seafood in a diverse range of dishes, and boy do they do it well! The atmosphere is also lovely.

After strolling around the Boston Public Gardens, you’re sure to be in need of a ride around the pond. Since 1877, there have been boats that sail the pond that are adorned with a swan body at the back of the boat.

If you decide to go for a ride, you’ll hop in the boat and be paddled around the pond by a tour guide who sits comfortably in the swan part of the boat. This can be a very peaceful and fun experience for the whole family!

Unfortunately, the boats are only in operation during the summer months. But that doesn’t mean that in winter you miss out on all the fun. The pond is only 3 feet deep, so it freezes over easily in winter and makes for the perfect ice rink.

Be sure to take a skate on the ice if you do happen to be staying in Boston during the colder months.

Day 1 / Stop 3 – Visit the Isabella Stewart Gardner Museum

• Why it’s awesome: The Isabella Stewart Gardner Museum is a woman’s personal collection of artworks that she and her husband collected throughout their lives.
• Cost: USD $15
• Food nearby: Wahlburgers is a famous burger joint starter by Mark Wahlberg and his brothers. They serve deliciously meaty burgers as well as a multitude of other delectable main courses. Be sure to try their spiked milkshakes if you’d like a creamy treat to get your buzz on!

The Isabella Stewart Gardner Museum is housed in the personal home of Isabella Stewart Gardner and shows off her personal collection of incredible artworks.

In the museum, you’ll find artworks from famed artists such as Botticelli, Titian, Fra Angelico, and John Singer Sargent, as well as many others.

When Isabella passed away in 1924, she instructed in her will that her house should be opened to the public as a museum. Unfortunately, in 1990 there was an art theft at the museum and 13 paintings were stolen. Amongst them were artworks from Rembrandt and Vermeer, as well as 11 others that were never recovered.

There is also a beautiful garden in the center of the museum, which is a lovely place to sit and relax, as well as taking a photo under the luscious vegetation.

Isabella was a Boston Red Sox fan, so anyone wearing Red Sox paraphernalia when visiting the museum gets a discounted entry fee. Discounts will also be given to anyone named Isabella!

Day 1 / Stop 4 – Visit Trinity Church

• Why it’s awesome: The original Trinity Church was built in 1733 but was burnt down in the famous Great Boston Fire. The current version was built shortly afterward to replicate the original.
• Cost: USD $10
• Food nearby: Eataly Boston is a fantastic collection of indoor restaurants that provides you with a wonderful selection of delicious Italian food. With one communal dining area, visitors can all get their meal from a restaurant that suits their preferences whilst still dining together. Expect a selection of wonderful pasta dishes, seafood delights and a wide selection of delicious comfort food.

Trinity Church is the first Romanesque style building to be built in Boston and makes a real statement in its surrounding area. The church is still operational to this day, as people go to worship every Sunday!

For a small entrance fee, you’ll get the opportunity to tour this Boston landmark and see the incredibly intricate architecture that makes this building so great!

The building is built in the shape of a Greek cross, which was truly unique for its time, and it features murals by the famed artist John La Farge. The stained glass windows were done by various different artists but remain a prominent feature of the beautiful church.

Trinity Church consistently ranks in the top 10 for America’s most significant architecture and is a wonderful sightseeing adventure.

If you’re a fan of statues, ornaments, paintings, and intricate architecture, be sure to add this amazing activity to your Boston itinerary.

Day 1 / Stop 5 – Take a Walk Through Little Italy

• Why it’s awesome: Little Italy is the oldest inhabited area in Boston and has the same feel as a quaint cobbled street in Italy.
• Cost: Free to explore!
• Food nearby: La Famiglia Giorgio’s Restaurant is a family-friendly restaurant that serves delectable Roman cuisine in healthy portions! If you’re looking for a wonderful mix of Italian seafood dishes and other hearty meals, then this is the perfect restaurant for you to visit during your time in little Italy. Be sure to add this wonderful restaurant to your Boston itinerary! If you have more time, you could even take a food tour of Little Italy in Boston !

Taking a stroll through the cobbled streets of Little Italy is one of the most amazing Boston points of interest. Many of the buildings in this area were built during the late 1600s and early 1700s, so they’re lots of fun to look at and to explore.

In the early 20th century, the area experienced an influx of Italian immigrants and remains the most popular place for Italians to frequent in the city.

The neighborhood has maintained its Italian character over the years and is now home to a variety of Italian restaurants, bakeries, and vendors.

On the last weekend of August every year, the area hosts The Feast of All Feasts , where you can experience vendors lining the streets selling wonderful smelling and tasting delights. If you’re not in the area during this time, there are still plenty of tasty treats for you in the surrounding restaurants and from vendors in the area.

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

Or, y’know… you can stick to just chucking it all in your backpack…

Bunker Hill Monument | USS Constitution Museum | Museum of African American History | Greenway Carousel | Boston Common

If you’re spending 2 days in Boston , you’re going to need more activities. You’ll climb a monument, visit two museums, ride a very unique carousel and end the day in Boston Common.

Let’s dig into day 2 of your 2 day itinerary in Boston!

Day 2 / Stop 1 – Climb Bunker Hill Monument

• Why it’s awesome: Bunker Hill was where the first battle between colonial and British forces took place in America.
• Cost: Free to visit!
• Food nearby: Monument Restaurant and Tavern serves delicious and unique brunch meals that will fill the hole in your stomach created by the invigorating climb to the top of Bunker Hill Monument. Enjoy a variety of comfort food options in a cozy setting that allows you to sit back and relax while indulging in your meal.

The Bunker Hill Monument was built in remembrance of the first bloody battle between colonists and the Britsh forces and stands an impressive 67 meters tall. After picking up a free climbing pass at the bass of the monument, you’ll be able to climb right to the top, which provides spectacular views of the beautiful city!

At the base of the monument, you’ll see a metal statue of Colonel William Prescott, who was the leader of the rebel forces. He was the one who gave the famed instructions “Don’t fire until you see the whites of their eyes”.

Although the British won that battle, it was a significant one that proved how much damage the rebels could inflict on them.

Climbing the monument is an activity you simply must add to your Boston itinerary as you’ll get the chance to enjoy panoramic views of the city below. Be sure to take your camera along for this activity as the sight is incredible!

Day 2 /  Stop 2 – Visit the USS Constitution Museum

• Why it’s awesome: The USS Constitution is the oldest commissioned naval vessel in the world that is still afloat.
• Cost: USD $10 – USD $15
• Food nearby: Brewer’s Fork is a cozy and rustic restaurant that serves delicious wood-fired cuisine. The pizzas are fantastic and the other dishes are very comforting! It’s the perfect place to stop off for lunch before heading to the next activity on your Boston itinerary!

The USS Constitution was commissioned by President Washington and set sail to the high seas in 1797. The ship is best known for defeating five British warships in the war of 1812. The ship now sits in the naval yard, and contains a whole host of wartime and maritime memorabilia, and serves the public as a museum.

Visitors are allowed to board the ship and explore the decks as well as take photos onboard.

The wooden-hulled ship is known lovingly by Bostonians as Old Ironside and matches the old-timey feel of Boston city as a whole.

If you care for a stroll around the navy harbor, it’s always an educational experience and is one of the best places to visit in Boston . You can take a guided tour of the harbor, or venture out on your own. Either way, you’ll have a learning experience second to none.

Day 2 / Stop 3 – Explore the Museum of African American History

• Why it’s awesome: The Museum of African American History is an informative museum that gives you the opportunity to learn about slavery and segregation in Boston.
• Food nearby: The Paramount serves American style comfort food in a cafe style diner that has a wonderful atmosphere. Tuck into a pancake stack, fluffy french toast or a juicy burger that will tantalize your taste buds.

The building in which the Museum of African American History is housed was built in 1835 as Abiel Smith School and was the very first public school in Boston for African American children.

It was used for this purpose for twenty years until in 1855, when African American children were integrated into all public schools.

The museum not only shows what the school was like when it was in operation but also what life was like as an African American individual during the 1800’s.

If you’re interested in the history of oppression in the city, then this museum is a must-see on your Boston itinerary.

The museum is part of the Black History Tour that is run in Boston, so if you’re planning on taking the tour, then give this activity a skip on the 2nd day of your Boston itinerary.

Day 2 / Stop 4 – Ride the Greenway Carousel

• Why it’s awesome: The Carousel is located in the Tiffany & Co Foundation Grove and is a fairly new addition to the grove.
• Food nearby: Fogo de Chao Brazilian Steakhouse is an upscale restaurant that serves a wonderful variety of delicious Brazilian cuisine. They specialize in meat dishes but also have a fantastic selection of vegetarian meals. If you haven’t tasted Brazilian cuisine, this is the perfect place to try it for the first time, so be sure to add this tasty experience to your Brazilian itinerary.

The Greenway Carousel is an activity that’s not only for kids but for adults too! The carousel contains a variety of different animals that you can ride, all of which are native to Boston. This makes the experience all the more unique and educational.

You can find lobsters, harbor seals, owls, grasshoppers, bunny rabbits, and eagles, as well as a whole hoard of other animals.

The carousel was designed with adults and children with physical disabilities in mind. So you’ll find it’s very easily accessible and has many features that make it a more inclusive experience.

Unfortunately, the carousel only operates on Fridays and Saturdays, so it’s great for a weekend in Boston , but you can visit on any day just to see what it looks like. Each animal on the carousel is a work of art, and worth going to see whether it’s on or not.

Be sure to take your camera along for this activity.

Day 2 / Stop 5 – Stroll the Boston Common

• Why it’s awesome : The Boston Common is the oldest park in America as it’s been in use since 1634.
• Food nearby: Pho Basil serves a mix of authentic Thai and Vietnamese cuisines. They serve a multitude of Vegetarian, Vegan, meat and fish dishes, so there really is something for everyone’s taste buds and dietary requirements. The meals are served in a generous portion which you’ll be very grateful for after a day of exploring and adventuring.

This 50-acre park is one of the most popular Boston landmarks as it’s visited by locals and tourists daily. We recommend visiting the Boston Common in the early evening when locals are on their way home from work, and often stop for chat or a vendor meal in the park.

The Boston Common was once a cow pasture, and then a British camp, before becoming an execution ground. Luckily for us, the area is a lot calmer now and has been used as a public park for almost 400 years.

The area is often used for public speeches, gatherings, protests, and concerts. Some of the most notable speakers to give a speech at the park were Martin Luther King Jr and Pope John Paul II.

This park is one of the stop-offs in the Freedom Trail, so you’ll see plenty of tour guides dressed in revolutionary period clothing.

HI Boston offers an incredible communal setting that leaves you feeling refreshed to start touring Boston every morning!

• Free Breakfast
• Reception (limited hours)

Freedom Trail | Black Heritage Trail | Boston Harborwalk | Harvard Yard | Mapparium

If you’re spending 3 days in Boston, you’re going to need a few more activities! Here’s what to do in Boston if you’re staying for a few more days!

Walk the Freedom Trail

• 5-mile walk
• 16 historically significant sites

The Freedom Trail is a wonderful activity to take part in during your time in Boston. Although there are many guided tours that take you along the Freedom Trail, it’s easy enough to take the tour on your own.

A series of bronze markers are embedded in the sidewalk, which point you in the right direction and allow you to follow them all 2.5 miles!

Along the way, you’ll get to stop-off at 16 historically significant sites, where you can learn a little more about the cities past before continuing along the route. The great part about taking a self-guided tour is that you decide where you’d like to spend the most time. You can also take a break to enjoy lunch at a restaurant or street-food vendor of your choice.

Most of the stops along the route are free to visit, which makes this great value for money as you’ll only have to pay admissions at 3 of the 16 sites (Paul Revere House, the Old South Meeting House, and the Old State House). If you’re on a tight budget, you can give these places a skip.

If you’re a history lover, then this activity simply must be added to your Boston itinerary!

Black Heritage Trail

• Boston walking tour
• 5 mile walk
• Beacon Hill neighborhood

The Black Heritage trail leads you down a 1.5 mile trail where you’ll get the chance to visit some of the most significant places in Boston relating African American history. The Beacon Hill neighborhood was home to Boston’s black population before the civil war.

After the civil war, the African American people staying in Beacon Hill were integrated into the rest of the city with all the other Bostonians.

Along the trail, you’ll visit the 54th Massachusetts Regiment Memorial which is situated in the Boston Common. You’ll also visit the African Meeting House, which was a secret meeting place for African American individuals before the civil war.

You’ll then visit the Lewis and Harriet Hayden House which is the home of the famed abolitionists. There you’ll learn about the plight of African Americans who were fighting for their rights. You’ll visit a few more sights, including the first public school for African American children.

There are tours that can lead you along the trail. These take place a few times a day and may offer extra insights into the past, however it is easy enough to take yourself on the trail if you’d like to save some cash!

Take the Boston Harborwalk

• 47 miles long
• Stunning views
• Activities along the way

The Boston harborwalk is something you have to do while you’re in the wonderful city! Although the walk is rather long and you probably won’t be able to walk all the way (especially in one day), you could hire a bicycle, or just complete part of the walk on foot.

It’s a wonderful way to end off the day, walking along the seaside while the sun sets. There are also plenty of activities to take part in along the way if you’d like to make a day of it.

While you enjoy stunning views of the city and the sea, be sure to stop at the USS Constitution, the Boston Tea Party Museum, the New England Aquarium, and the Institute of Contemporary Art.

End your day of exploring at Castle Island, a piece of Boston that juts out into the ocean and contains many of the best restaurants, cafes and high-end shops in the city.

If walking that distance seems a little intimidating, why not take a boat ride or a cruise along the shoreline to experience the route from a different perspective. If you’re spending more than a week in Boston, be sure to complete the route before you leave as it’s quite an accomplishment! It will leave you with some great memories and magnificent views etched into your memory.

Explore Harvard Yard

• The oldest part of Harvard University
• The central hub of Harvard
• Surrounded by attractions

The Harvard Yard is the central hub of the university, and is a great place to pick up on the atmosphere of this incredibly diverse school. Here you’ll find students playing outdoor games, whether it be a game of frisbee or a quieter game of chess.

In the Harvard Yard, you’ll see the John Harvard Statue to commemorate one of the founders of the university in 1638. The statue is made of bronze and serves as an integral part of the yard.

The Harvard Yard is the oldest part of the university and is surrounded by the Harvard library as well as the Memorial Church. The area opens up into the Harvard square, which consists of restaurants, bars and shops which are continually filled with cheerful students from the university!

You can roam this area of the campus as you please, and explore the different buildings that make up this wonderful university. Guided campus tours are lead by the students of the university at different times throughout the day. However, you can easily take yourself on a self-guided tour of the area!

See the Mapparium

• See the world globe without distortion
• Built in 1935
• Three-story map

The Mapparium can be found in the headquarters of the Christian Science Monitor. It’s a huge glass globe the size of a three-story building. To view the globe, you step inside and view it from the inside.

The Boston Mapparium is the only place in the world where you can see the entire globe without a distorted perspective. If you stand in the middle of the floor, your eyes will be equidistant to every point on the map, allowing you to see the globe for the first time, as it really is.

The globe was built in 1935 and lights up so that you’re able to see each point accurately. The perfect spherical shape of the globe allows this masterpiece to be a whispering gallery too. If you whisper into one side of the globe, another individual will be able to hear you at the opposite end of the globe.

In order to enter, you’ll have to take a guided tour which takes place every 20 minutes. Be sure to check the tour times before venturing out to the awesome Boston attraction.

If you’re a fan of geographical artifacts, this is a wonderful thing to do. Although some of the names of the countries are a little out of date, you’ll still find it to be very geographically accurate!

For the most part, Boston is a fairly safe place. However to pass a safe vacation in Boston you should excercise some precautions. In recent years, theft has become a bit of a problem in recent years so it’s important not to avoid “run down looking” neighbourhoods.

Crime tends to increase at night in quiet areas, so be sure to stick to the more populated areas if you find yourself out and about during the evening.

Smoking in Boston is forbidden in most areas! To ensure you don’t get into trouble with the law, make sure you don’t start lighting up just anywhere. There are actually only a handful of places you’re allowed to smoke, so be sure to check for a sign stating you’re allowed to smoke before lighting that cigarette.

If you’re visiting Boston in winter, it’s important to be prepared. Bring shoes with rubber soles and warm jackets as it can snow at any time during the winter months. You don’t want to get caught in a sleet storm unprepared!

Don’t Forget Your Travel Insurance for Boston

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

If you’re spending a little more time in this wonderful city, you should consider taking a few day trips from Boston . Here are a few of our favorite day trips that you should be adding to your Boston itinerary!

Boston Duck Tour

The Duck is a unique amphibious vehicle that allows you to discover Boston from a completely different perspective. A duck is a vehicle that was used during World War II to travel on both land and in the water.

You’ll start off touring the historic streets of Boston before plunging into the Charles River, where you’ll enjoy an 80-minute tour of the city. Along the way you’ll get the chance to learn about the unique heritage of the city that gave birth to freedom in America.

All this while enjoying splendid views of the city from the perspective of the water!

Guided Tour of Fenway Park

Fenway Park is home to the beloved Boston Red Sox Baseball Team. On this guided tour, you’ll learn about the stadium which is now over 100 years old and about it’s famous home team.

You’ll learn about the many unique features of the Fenway Park Stadium and about the careers of some of its very best players. You’ll also browse the stadiums 170,000 artifacts and over 150,000 photographs.

If you’re a sports fanatic, this tour is the perfect one for you while you’re visiting Boston.

The Boston Tea Party Interactive Day-Trip

During this Boston day-trip, you’ll get the opportunity to go back in time, and learn about the Boston Tea Party , which triggered the American Revolution. The Boston Tea Party was a protest against unfair taxes, so you’ll get the chance to throw tea overboard to recreate the actions of the sons of liberty.

Along the way, you’ll see holographic characters that will teach you about the events that triggered the American Revolution. You’ll also explore a replica of 2 of the Tea Party Ships that belonged to the Dutch East India Company.

Boston Guided Trolley Tour

On this trolley tour, you’ll travel past 120 of the best sightseeing highlights in Boston. You’ll travel through Beantown from Little Italy, all the way through to the waterfront. Be sure to take an amble around the waterfront as there are a myriad of awesome restaurants and wonderful shops to explore.

You’ll be able to stop for photos at any point along the route, so be sure to bring your camera along for this adventure!

You’ll follow along the freedom trail, stopping off at many of its main attractions before the tour comes to an end.

Martha’s Vineyard Day Trip and Island Tour

Take this day trip from Boston that gives you the opportunity to travel to Martha’s Vineyard without the hassle of booking land and ocean transport.

On the tour you’ll see the homes of many famous celebrities, a gingerbread house and America’s oldest carousel. All of which are great sightseeing opportunities.

Enjoy magnificent views as you travel through the water to the wonderful island. You’ll visit all 6 towns on the island before hopping back on a ferry and heading back to Boston. The tour is all-inclusive so snacks and lunch will be provided during the day.

Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

It looks exactly like a normal belt  except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

Find out what people want to know when planning their Boston itinerary.

What should you include on a 3 day Boston itinerary?

Make sure to check out these Boston hotspots: – Little Italy – Bunker Hill Monument – Boston Common – Black Heritage Trail

Where should you stay for a weekend in Boston?

Back Bay is a great option if you’re short on time as it offers easy access to top attractions. For nightlife, base yourself downtown.

What can you do in one day in Boston?

Walking the Freedom Trail (or part of it) is a great way to see Boston’s top historical attractions. Head to Little Italy for food, and chill out in the Public Garden.

Are there any good day trips from Boston?

There are plenty of Boston trips to choose from. Hop on a Boston Duck Tour, a guided Trolley Tour, or head out to Martha’s Vineyard for an island tour.

Boston being one of the oldest cities in the United States has so many heritage sights to see and history lessons to learn. Although the city does have a dark past, Boston is also the birthplace of freedom in America.

Boston leaves little for the heart to desire as it provides sea-side views, as well as a vibrant city life that is comparable to that of the hustle and bustle of New York.

Stroll through the waterfront in the morning and spend the evening exploring the thriving nightlife in Boston, before heading back to one of the best places to stay in Boston.

No matter what your vacation preferences are, this holiday is sure to blow your mind and keep you coming back.

So what are you waiting for? Start booking the most exciting tours in Boston for your travels! Can you hear it? The hustle and bustle of Boston’s city life is calling your name!

Made it this far? You get 15% OFF to book a place to stay ! Offer valid exclusively for Broke Backpackers 😉

Mary Beth Skylis

Share or save this post

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Save my name, email, and website in this browser for the next time I comment.

Notify me of followup comments via e-mail.

Protect Your Trip »

The 15 Best Boston Tours

Get to know one of America's most historic cities with these tours.

Getty Images

Hoping to experience Boston through the eyes of a local? A guided tour may be just the thing. Factoring in traveler sentiment and expert opinion, U.S. News selected some of Boston's best tours. Whether you're eating your way through the North End or zipping around Boston Common on a Segway, you'll see this New England city in a new light and learn some of its history along the way during these top Boston tours.

The Revolutionary Story Tour

Price: Adults from $76; kids from $38 Duration: 4 hours

Many reviewers call this tour enjoyable and one of the best walking tours they'd ever been on thanks to the engaging guide. Led by a local resident with degrees in history, political science and public policy, the tour takes visitors through the streets of Boston to chronologically retell the story of the American Revolution. Along the 3.5-mile jaunt, you'll pass by a dozen of the sites featured on the Freedom Trail, and you'll also hear about the key players in 18th-century Boston, including John Adams, Benjamin Franklin and Paul Revere.

Tours are offered daily at 9:30 a.m. There is also a 1:30 p.m. tour Thursday through Sunday during the winter months and daily during the summer months through the beginning of November. There is a maximum of 16 people per tour. The company partners with another local guide to provide private tours.

Check prices & availability on:

City Experiences by Hornblower – New England Aquarium Whale Watch Cruise

Price: Adults from $65; kids from $45 Duration: 3.5 hours

Hop on one of City Experience's high-speed catamarans for a whale watching excursion to the Stellwagen Bank National Marine Sanctuary. This area is a magnet for whales, dolphins, sea birds and other marine creatures who head there to feed. New England Aquarium naturalists on board offer their insights on whales, answer questions and explain whale behaviors, a big plus for travelers. During your trip, you may see several different species of whales, including humpbacks, finbacks, minkes, sei whales and endangered right whales.

Tours leave from mid-May through early-November from Long Wharf, which is located near the aquarium. Tour frequency depends on the month, but there is at least one per day. Cruisers say the tour is fun and report seeing plenty of wildlife. Combo tickets that include admission to the aquarium are also available. The company also offers sightseeing and sunset cruises.

CityView Trolley Tours

Price: Adults from $42; kids from $20 Duration: 1 hour

The family-friendly hop-on, hop-off CityView Trolley Tours offer a convenient and comfortable way to explore the city and visit its top attractions , something visitors (especially those in Boston for the first time) appreciate. Stops at the New England Aquarium, Quincy Market and Old North Church, among others, make it easy to access sites along the Freedom Trail and other neighborhoods. What's more, guides share fun and informational tidbits along the way.

Trolleys run daily from mid-April to November from 9:30 a.m. to 4:30 p.m. Note: While you can hop on and hop off the trolley as you please, tickets are only valid for one full tour loop. Two-day passes are also available.

Old Town Trolley Tours – Boston Hop-On Hop-Off Trolley Tour

Price: Adults from $50; kids from $29 Duration: 1.5 hours

Explore the top sights in Boston on this hop-on, hop-off trolley tour that makes 18 stops. Along the route, you can hop off and explore attractions like Faneuil Hall, the "Cheers" bar, the USS Constitution and the Old State House, and then hop back on at your leisure. Without getting off, you'll tour for about 90 minutes. Trolleys frequently stop approximately every 15 minutes. Participants praise the convenience this tour offers and rave about the entertaining, informative guides. Reviewers also say the tour is a great way to see the city without having to do a lot of walking.

Trolleys run daily from 9 a.m. to 4 or 5 p.m., depending on the time of year. For one-day tours, tickets allow for unlimited re-boarding. Tickets also get you discounted rates for a Boston Harbor cruise as well as discounted entry to the Boston Tea Party Ships & Museum. Two-day tickets, as well as the Ghosts & Gravestones evening tour are also available.

Boston Pizza Tours – North End Pizza Tour

Price: From $49 Duration: 2.5 hours

Sink your teeth into some of Boston's best pizza on this walking tour. You'll start your stroll in North End, which is considered Boston's Little Italy. Along the way, you'll pass by five sites on the Freedom Trail, including the Paul Revere House and the Old North Church. The tour cost includes three full-size pizza slices, water and a cannoli. Tourgoers applaud guides for their positive attitudes and entertaining, educational delivery of Boston history. Reviewers are also complimentary of the food.

Tours are generally offered two times daily at 11 a.m. and 2 p.m., but a 5 p.m. tour is offered during certain months of the year. Tours are capped at 12 participants. The tour can accommodate vegetarian diets; those with other dietary restrictions (such as vegan diets or food allergies) will need to take a private tour.

Fenway Park Tours

Price: Adults from $25; kids from $17 Duration: 1 hour

Baseball fans and history buffs relish the chance to take a behind-the-scenes peek at America's oldest ballpark. Even non-baseball fans find the tour worthwhile, according to reviewers. The tour takes visitors to important sites within the ballpark, including the world-famous 37-foot-high Green Monster. The excellent guides, full of Red Sox and Fenway Park trivia, offer an entertaining tour and are a hit with participants.

Tours run year-round from 9.m. to 5 p.m. (at 10 a.m. November through March) and start on the hour. On game days, the last tour is scheduled three hours before game time. Fenway Park also offers a variety of other stadium tours, including Day Game Premium Tours and Fenway in Fifteen, a condensed 15-minute tour.

Courtesy of Rose Kennedy Fitzgerald Greenway

Boston Segway Tours

Price: From $69 Duration: 1 or 2 hours

Boston Segway Tours takes visitors on an adventure through the city. Since it's faster to glide than walk, you can cover much more ground on Segway than by foot. As you travel from Boston Common to the Rose Fitzgerald Kennedy Greenway, your guide takes you by some of Boston's most famous landmarks while always keeping an eye out for riders' safety, according to tour-takers. Pick a two-hour tour to visit Cambridge.

Participants must be 14 or older and weigh at least 100 pounds to ride; additional restrictions may apply.

Urban AdvenTours – City View Bike Tour

Price: From $60 Duration: 3 hours

Exploring Boston by bike is a great way to cover a lot of ground in an exciting, active way. Urban AdvenTours' flagship City View Bike Tour takes participants on a 10- to 12-mile trek through six different neighborhoods. You'll bike through major Boston sites, such as North End, the Boston University campus and Kenmore Square, Fenway Park, the South End, Boston Common and Long Wharf. Along with the comprehensive overview of the city, riders commend the care guides take in making them feel safe.

This tour rides daily at 10 a.m., with additional 2 p.m. departures on Saturday and Sunday during the summer months. The tour is best for those comfortable riding on city streets. Children must be age 10 or older. Adults can upgrade to an electric bike for an additional fee. Urban AdvenTours also offers cycling trips through Cambridge and the Emerald Necklace park system, as well as a family-friendly tour for kids 10 and younger.

Off the Eaten Path Tours

Price: Adults from $95; kids from $40 Duration: 3 hours

On this food tour of the North End – Boston's famous Italian neighborhood – owner Paula Noukos promises more than just samples of tasty food. Besides stopping at popular spots, such as Bricco Panetteria and Galleria Umberto, you'll hear tips on how to shop for the best extra virgin olive oil and balsamic vinegar. You'll also learn about the history and architecture of this unique neighborhood, a highlight for reviewers. Travelers are also fond of the guide and appreciate her vast knowledge of the neighborhood.

Tours are generally offered Tuesday through Saturday at 11 a.m. and are limited to 12 people.

Courtesy of Boston Duck Tours

Boston Duck Tours

Price: Adults from $53; kids from $38 Duration: 80 minutes

Quack and splash your way around Beantown with the entertaining Boston Duck Tours, which takes passengers around Boston and into the Charles River on World War II-style amphibious landing vehicles. On the tour, entertaining "conDUCKtors" keep up a lively patter, describing neighborhoods, Boston history, architecture and trivia along the way. A highlight for many visitors is when the vehicle heads into the river offering a different perspective of the city.

Ticket discounts are available for seniors and children 2 and younger. Tours depart from the Museum of Science, the Prudential Center and the New England Aquarium several times a day from mid-March through early-December.

Boston Crawling – Independence Pub Crawl

Price: From $75 Duration: 2 hours

Sip your way through the city at four historic watering holes on Boston Crawling's Independence Pub Crawl. On this tour, you'll visit pubs that have historic significance, drink local brews and hear Boston's "secret" history as you barhop along the Freedom Trail. Reviewers say the tour is informative and fun and applaud the beer recommendations provided by the guides.

Participants can take tours daily at 3 and 7 p.m. There is also an additional noon tour on the weekends. Tourgoers must be at least 21 years old, regardless of whether they're drinking. Tickets include four draft beers of your choice. If you prefer to purchase drinks as you go, you can purchase tickets for a lesser price.

PhotoWalks Tours of Boston – Freedom Trail

Price: Adults from $45; kids from $20 Duration: 1.5 hours

Explore the historic sites of the city and refine your photography skills at the same time on this tour. In addition to visiting Freedom Trail landmarks, such as Boston Common, Park Street Church, the Granary Burying Ground and the Boston Massacre Site, you'll also learn expert tips on how to use your camera or smartphone to take the best pictures – a highlight for many participants. Reviewers are also complimentary of the insightful guides.

Tours run Tuesday, Thursday and Saturday year-round at 1 p.m. The tour is capped at 10 participants, but maybe more during peak times of the year. If you're interested in exploring other neighborhoods or topics, you can sign up for one of PhotoWalks' other tours, including Beacon Hill and the North End, among others.

Courtesy of the Freedom Trail Tour

Freedom Trail Tours – Walk Into History

Price: Adults from $17; kids from $8 Duration: 1.5 hours

The nonprofit Freedom Trail Foundation leads the way on this tour of the Freedom Trail – a milelong path that weaves past some of the city's most historic sites. A costumed guide, in character, leads you to 11 sites, including Boston Common, King's Chapel, the Old South Meeting House, the Boston Massacre site and Faneuil Hall. Reviewers rave about the guides and the characters they inhabit, and highly recommend this excursion over a self-guided tour of the Freedom Trail.

Tours are given daily at 11 a.m., noon and 1 p.m. Other themed tours, including tours that focus on the women of the Revolutionary War and African American patriots, are also available.

Boston Foodie Tours – Boston Public Market & North End Tour

Price: From $90 Duration: 3 hours

Boston Foodie Tours explores two of Boston's famous mainstays: The North End and the Boston Public Market. After enjoying pizza, cannoli and bread in the North End, you'll wind your way to the market to sample doughnuts and ice cream, among other treats. Your tour concludes with a tasting of clam chowder and cornbread. Past tourgoers say this is a must-do experience while visiting Boston.

Tours run Tuesday through Saturday at 10:30 a.m. and 11:30 a.m. on Sundays. Tours are not given on major holidays. The company also offers a comprehensive tour of the North End, plus a private foodie outing to Beacon Hill, among other options.

City Brew Tours – Boston Signature Brew Tour

Price: From $89 Duration: 3.5 hours

For an in-depth Boston beer education, City Brew Tours' Signature Brew Tour is a great place to start. During the tour, you'll be chauffeured around the city in a comfortable van, visit three craft breweries, get behind-the-scenes tours and enjoy up to 12 different local craft beers and a snack along the way. Tourgoers laud the knowledgeable guides and love that driving isn't an issue.

City Brew offers this tour Wednesday through Sunday. Outings depart at 4:45 p.m. and 5:30 p.m. on Wednesday and Thursday. Friday through Sunday, tours begin at noon. All participants must be 21 or older to tour. Tours are capped at 14 participants. A Boston Brew Mystery Crawl is also offered, as are private tours.

You may also be interested in:

• The Best Hotels in Boston
• The Best Whale Watching in Cape Cod
• The Best Weekend Getaways in New England
• The Best Historical Cities to Visit in the USA

Tags: Tours , Boston , Travel , Vacations , food and drink , New England Vacations , US Vacations

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

If you make a purchase from our site, we may earn a commission. This does not affect the quality or independence of our editorial content.

You May Also Like

The best sedona tours.

Amanda Norcross Aug. 15, 2024

The Best Grand Canyon Tours from Vegas

Taylore Fox Aug. 13, 2024

The Top Places to See Fall Foliage

Gwen Pratesi and Erin Vasta Aug. 13, 2024

11 Best Niagara Falls Tours

Lyn Mettler and Amanda Norcross Aug. 12, 2024

The Best Movie & TV Tours

Timothy J. Forster Aug. 8, 2024

Best New Orleans Swamp Tours

Amanda Norcross Aug. 8, 2024

The Best Pearl Harbor Tours

John Rodwan and Amanda Norcross Aug. 8, 2024

The Best Vatican Tours

Lyn Mettler Aug. 8, 2024

The Best Stonehenge Tours

Kim Foley MacKinnon and Ann Henson Aug. 7, 2024

The Pros & Cons of Using a Travel Agent

Amanda Norcross Aug. 7, 2024

Budget Travel With Gabby

Travel tips, budget travel guides, volunteering stories, more!

21 Best Day Trips From Boston, Massachusetts

Here are my favorite day trips from Boston, MA, ranging from cities and charming seaside towns to national parks, state parks, and more!

Because I was born and raised in Massachusetts, I’ve spend much of my life exploring New England .

Though exploring my home didn’t excite me as much as going overseas, I have grown to love and appreciate the beauty and charm of New England.

So I’ve decided to write a post about the best day trips from Boston, MA.

Boston is one of the USA’s most incredible cities. It’s packed with history, architecture, museums, nightlife, and lots of cool attractions .

If you’re visiting Boston and you’d like to escape the city for a day, here are some beautiful day trips from Boston. I’ll also include some fun weekend getaways at the end!

Save money on Boston’s top attractions with the Boston City Pass !

How To Get Around On Day Trips From Boston

I would like to note that public transportation in the US is not great. There are some buses and trains, but having a car is the best way to get around.

Consider renting a car for the day if you want to visit one of these places. You don’t need a car in Boston itself though. Parking is expensive and honestly, Boston is a nightmare to drive around.

But if you want to leave the city and explore more of New England, it’s worth renting a car!

There are also some day trips from Boston without a car such as Salem, York, Plymouth, and Martha’s Vineyard. For these destinations I’ll link to some guided day trips that include transport.

That saves you the hassle of driving and navigating on your own!

What are the best day trips from Boston?

From Martha’s Vineyard and Cape Cod to some lesser known New England destinations, here are some of the best day trips from Boston!

Whether you want forest, beach, historic villages, or classic New England towns, there is lots to see and do outside the city.

Visit iVisa.com to apply for your visa for the USA!

1. Bolton, MA

• 40 minutes from Boston

Bolton is a peaceful residential town in Central Massachusetts. This is near where I grew up, and there is actually a lot to do here!

Pick your own apples in autumn at Bolton Spring Farm. Or visit Bolton Orchards for that classic rural New England farm stand. Here you can drink fresh apple cider, grab a homemade sandwich at the deli, or get an ice cream from the cafe.

Or if wine is more your style, head to Nashoba Valley Winery for wine tasting and nibbles outside overlooking the countryside.

2. Salem, MA

Located a short drive north of Boston, Salem is a historic Massachusetts town made famous by the Salem Witch Trials of the late 1600s.

A day trip to Salem from Boston allows you to explore the area’s rich maritime history through museums, landmarks, and historic sites around town.

The best way to learn all the fun facts about Salem is on a guided night walking tour ! You can also book a day trip from Boston to Salem via ferry that includes a visit to the Witch Museum. This is one of the best day trips from Boston without a car.

3. York, ME

• 1 hour from Boston

At just over an hour drive from downtown Boston, York is a beautiful seaside town in Maine.

Here you can enjoy the beach, tour a brewery or distillery, go golfing, and get ice cream or lobster rolls at a local restaurant. Be sure to also check out the iconic Nubble Lighthouse.

Book this highly-rated day trip from Boston that includes the highlights of Maine’s south coast such as York, Kennebunkport, and Ogunquit.

4. Purgatory Chasm State Reservation, MA

Located in Sutton, Massachusetts, Purgatory Chasm is a great place to stretch the legs outside Boston.

Full of huge rock formations, lush forests, and walking trails, this place is perfect for nature lovers and families.

But the rocks can be slippery in snow, rain, or ice, so avoid hiking in winter or wet weather.

Parking is $5 for MA residents and $20 for non residents.

5. Newport, RI

• 1 hour and 45 minutes from Boston

This charming Rhode Island city is one of the coolest places to visit in New England.

Known for its historic mansions, fun nightlife, cool shops, and beautiful coastline, there is so much to do in Newport.

Check out the unique shops on the historic Thames Street or go on a scenic boat cruise in Narragansett Bay. Stroll along the Cliff Walk or surf at Easton’s Beach.

Check out my full list of the best things to do in Newport here !

6. Douglas State Forest, MA

• 1 hour and 15 minutes from Boston

A beautiful place to escape into nature near Boston is Douglas State Forest .

The state park is open sunrise to sunset, and parking fees are charged between May and October for $9 (MA residents) or $30 (non-residents).

Douglas State Forest offers all sorts of outdoor activities including hiking, swimming, boating, horseback riding, fishing, bird watching, mountain biking, or cross country skiing and snowshoeing in winter.

7. Hampton Beach, NH

One of the best places for a beach day near Boston is Hampton Beach, New Hampshire.

The long strip of golden sand is framed by a lively boardwalk packed with eateries, arcades, souvenir shops, and entertainment venues.

It’s a popular spot for surfing as well, though the water is always freezing cold! You can also go swimming, walking, fishing, exploring, and camping at Hampton Beach State Park .

8. Cape Cod, MA

• 1-2 hours from Boston

Often referred to ask the “arm of Massachusetts”, Cape Cod is the peninsula that juts out into the Atlantic Ocean from the state’s eastern side.

A popular holiday spot and retirement destination for Massachusetts locals, Cape Cod is known for its charming towns, sandy beaches, and laid-back coastal vibe.

Cape Cod is packed with bustling towns like Falmouth, Mashpee, Hyannis, Bourne, Chatham, and Provincetown. Though every corner of the Cape has something special about it.

Flanked on both sides by sand dunes and beaches Cape Cod offers plenty of places to relax on the sand, swim in the sea, bike along the shore, and go on whale watching cruises .

Cape Cod National Seashore is a protected area of coastline where you can explore historic lighthouses, wildlife-filled marshes, and biking trails.

9. Old Sturbridge Village, MA

• 1 hour and 10 minutes from Boston

Whether you’re a history lover or you’re traveling with kids, Old Sturbridge Village is an educational and interactive place to visit near Boston.

Old Sturbridge Village is like a living museum! Wander through the sprawling replica of a rural Massachusetts town from the 1830s and learn what life was like back in the day.

10. Providence, RI

The exciting capital city of Rhode Island is just 1 hour from Boston!

A day trip or even a weekend trip to Providence is well worth it because this city is packed with entertainment and culture.

Visit a museum, explore a local art market, go on a ghost tour , or indulge in the nightlife. I’ve had so many fun experiences in Providence over the years and it’s truly an awesome city.

11. Keene, NH

• 2 hours from Boston

Keene is a quaint town in southwest New Hampshire that also makes a nice day trip from Boston.

Known for being a college town, Keene has a walkable town center full of classic New England architecture, cute cafes, green spaces, and nice restaurants.

There are also some great hiking trails around Keene, such as Mount Monadnock.

Harry Potter nerds should consider visiting Keene during the last week of July, also known as “Keene Wizarding Week”, when all the local businesses around town have Harry Potter-themed events and decorations!

12. Plymouth, MA

Plymouth is known for being the arrival point of the pilgrims who came over from England in 1620. It’s where the first European Settlement in New England began, thus playing an important role in US history.

Tourists flock to Plymouth to see the famous Plymouth Rock and the exact replica of the Mayflower II, the ship that the pilgrims arrived on.

Plymouth also has cool museums, gardens, walking trails, forests, and even a winery.

You can book a day trip to Plymouth if you’re looking for day trips from Boston without a car! This includes Boston hotel pick-up, guided tours around the historical sites, and a stop in Quincy (another historic Massachusetts town where 2 US presidents were born).

13. Walden Pond, MA

• 30 minutes from Boston

Located in Concord, Massachusetts, Walden Pond is one of the easiest day trips from Boston.

Here you can stroll through the peaceful nature, swim in the pond, or try water sports such as kayaking, canoeing, or boating.

Walden Pond became famous when Henry David Thoreau wrote an entire book about the beauty of nature here (the book was titled Walden ).

So if you’re looking to escape the city and really dive into the natural beauty of Massachusetts, Walden Pond is the place to go.

14. Kittery, ME

Kittery is an adorable coastal town located near Maine’s southern border.

With pebbly beaches, cozy seafood restaurants, and unique museums, Kittery has lots to offer day trippers from Boston.

Go bike riding around the historic Fort Foster and eat a Maine lobster at Chauncey Creek Lobster Pier. Or shop for local produce at the Kittery Community Market on Sundays.

Go for a chilly ocean swim at Crescent Beach or Seapoint Beach. Kittery has lots of places to get outside and soak in the salty, seaside air!

15. Plum Island, MA

A beautiful barrier island located off the coast of northern Massachusetts, Plum Island is the perfect summer getaway from the city.

It’s about 11 miles long and filled with soft sandy beaches, lobster shacks, and the protected ecosystems of the Parker River National Wildlife Refuge.

Sandy Point State Reservation is also a great place for bird watching, sunbathing, and exploring the peaceful nature.

16. Portland, ME

Portland is a super cool city in Maine that is one of the best day trips from Boston.

This small city has new art galleries, ice cream shops, live music venues, dispensaries, museums, and more popping up all the time.

Grab a brew at Allagash Brewing Company, enjoy the views at the Portland Head Lighthouse, or check out the Portland Museum of Art.

Take your sightseeing to the waters with a scenic cruise , or cover more ground on a historic trolley tour !

More Day Trips From Boston (Better Suited To Weekend Trips)

There are so many amazing places to visit on a weekend trip from Boston, including New York City and Acadia National Park. These are about a 4 hour journey from Boston though, so you probably wouldn’t want to do these as a day trip.

However, here are some more epic locations that could be done as either a day trip or a weekend getaway.

The drive is around 2-3 hours for all of these. So you’d be better off on a weekend trip unless you want to wake up early and smash out lots of driving in one day.

Use Skyscanner to find the cheapest flights around the US!

17. Martha’s Vineyard, MA

• 2 hours and 45 minutes from Boston

Martha’s Vineyard is an iconic Massachusetts getaway. It’s a bit of a mission to get there from Boston, which is why it’s better suited to a weekend trip.

Travel by car, bus, or ferry to Wood Hole in Falmouth, Cape Cod. Then catch the ferry over to Martha’s Vineyard.

Or book a convenient day tour from Boston that includes all your transport so you can visit the island without all the hassle.

Once you arrive, spend the day strolling through the little town center, where there are quirky stores, seafood restaurants, fudge shops, and plenty of other cute attractions.

The colorful, intricate, fairytale houses of Oak Bluffs Campground are a highlight of Martha’s Vineyard as well!

18. White Mountains, NH

• 2.5 hours from Boston

The White Mountains in New Hampshire are a haven for wilderness lovers.

Filled with towering peaks, challenging trails, epic gorges, quaint mountain towns, and more, this located offers a wholesome getaway from the city.

Flume Gorge is a super cool attraction to check out. For those classic New England fall foliage views, visit the White Mountains in October or November!

Read my complete hiking guide to Flume Gorge for more info.

19. Block Island, RI

• 3 hours from Boston

This tiny but fun island off the coast of Rhode Island is another top beach destination in New England.

Admire the sand dunes at Mohegan Bluffs, hike along the Clay Head Nature Trail, or admire one of the few adorable lighthouses.

Block Island is also filled with beaches, restaurants, bars, and cozy inns if you want to stay the night.

20. Nantucket, MA

• 3.5 hours from Boston

Nantucket is another stunning island that you can get to in a few hours from Boston!

You’ll need to get yourself to Hyannis in Cape Cod and then catch the ferry from there. Consider combining Nantucket into a weekend trip to Cape Cod if you want!

Top things to do on Nantucket include strolling the Sconset Bluff Walk, seeing Brant Point Lighthouse, and visiting the Whaling Museum.

And of course, hitting the beach. Sconset Beach, Jetties Beach, Madaket Beach, and Steps Beach are top choices.

21. Lake Winnepesaukee, NH

One of the top destinations for a weekend trip from Boston is Lake Winnepesaukee, the largest lake in New Hampshire.

Nestled at the foothills of the White Mountains, New England locals flock here in summer for boating, swimming, and enjoying that lazy lake life.

Popular beaches on Lake Winnepesaukee include Weirs Beach, Bartlett Beach, and Allen Albee Beach.

Other highlights of the area include the local museums, riding the Winnepesaukee Scenic Railroad, seeing a movie at the Weird Drive-In Theatre, and playing games at Funspot Arcade .

Thanks for reading about my favorite day trips from Boston, MA!

For anyone traveling to the USA, check out my list of 50 budget travel tips to save money. The USA isn’t a very cheap country to travel around!

I also definitely recommend having travel insurance. The healthcare system in the USA is insane, and if something bad happens you may just go bankrupt trying to pay for emergency care out of pocket.

Check out my budget traveler’s guide to travel insurance for more info. Or check out my favorite travel insurance website, Squaremouth Insurance !

You also need a visa to visit the USA! Don’t forget to apply before you arrive.

This post may contain affiliate links. Read more about this in my About Me page!

Share this:

Leave a Reply Cancel reply

Discover more from budget travel with gabby.

Subscribe now to keep reading and get access to the full archive.

Type your email…

Continue reading

23 Fabulous Things To Do In & Around Boston This October

This year's Boston October events are filled with spooky spectacles, fall foliage and of course, abundant apple picking.

As the temperature drops and the leaves change colors, Boston is looking positively picturesque at this time of year. And with Halloween just around the corner , there are tons of activities to take part in around the city this October!

From festivals to nature walks, here are our recommendations for plans this month:

1. Visit Michelangelo’s Sistine Chapel: The Exhibition

Admire the timeless works of Michelangelo magnified 60x! The global exhibition will finally make its way to Boston this October after successful runs in London, Toronto, Shanghai, and NYC! Guests can experience Michelangelo’s iconic frescoes up close and personal with vivid detail.

Learn more and get tickets here !

Find it at 121 Webster Avenue, Chelsea, MA 02150

2. Take a spooktacular mystery picnic with friends

What is a distinguishes a foodie from a mere mortal?

Enjoy the ultimate foodie adventure as your taste buds, and mind get to experience the thrill of a mystery picnic. Solve clues that’ll lead you to your ultimate destination where an extravagant picnic awaits! Reserve your adventure online .

3. Light up the mood with a candlelight concert

Imagine sitting in the warm glow of a thousand candles, with a live orchestra softly strumming classic tunes in an ornate historic building. Candlelight Concerts mesh the magic of live performance with a multi-sensory musical experience for a jaw dropping performance!  October brings two unique Candlelight experiences to Boston.

• If you’re in for a spine-chilling musical performance, check out the Haunted Evening of Halloween Classics !
• If you’re a Swiftie you’ll love Candlelight: A Tribute to Taylor Swift at First Church for the ultimate fall vibes

These limited-edition Candlelight experiences only take place in October! Tickets are selling out fast for showtimes, so make sure to secure a seat !

4. Go apple picking at a tranquil orchard

Apple picking is the quintessential fall activity in New England. What’s better than exploring picturesque apple orchards, picking your own, and taking a bag home to enjoy in a homemade apple pie or just by themselves? Our list of the ten best orchards will definitely get you motivated to plan a weekend excursion outside the city.

• Brooksby Farm in Peabody
• Boston Hill Farm and Smolak Farms in North Andover
• Lookout Farm in Natick
• Dowse Orchards and in Sherborn

If you want a pick at some of the best apples in the country, according to USA Today, then head to this farm in Northborough, MA!

5. Explore Massachusetts’ spookiest town, Salem

Just 17 miles north of Boston sits the small, quaint town of Salem: a place known for its ghosts, mysterious energy and, of course, its famous witch trials. From haunted spots and historic sites to magic shops, we’ve come up with a few magical Salem spots to explore and bask in the city’s witchy spirit. Check out our full guide to exploring Salem here.

You can also try your own stay in the Sanderson Sisters’ cottage starting on October 12; read more about that here!

6. Catch the fall foliage at the best rated spot in Massachusetts

Planning a trip to the countryside to catch the leaves changing colors this fall? Lenox, MA should be on your itinerary. According to Reader’s Digest , this Berkshire town has some of the most vibrant fall foliage in the country. Starting in late September, the area’s landscapes are ablaze with reds, yellows, and greens. Read more here.

7. Or explore a hidden waterfall in Vermont, surrounded by changing trees

Tucked away in Warren, VT, these falls are the perfect natural spot to escape the leaf-peeping crowds. A wild swimming spot may not sound like the most appealing fall destination but hear us out. If you’re looking to escape the throngs of leaf-peepers currently exploring the New England wilderness but still want to bask in the glorious fall foliage of the area, this is the place for you this fall. Details here!

8. Get lost in a corn maze

Before escape rooms were all the rage, corn mazes were (and still are!) the best places to have fun and solve a massive outdoor puzzle with your friends. Bring family and friends for a day of trial and error as you navigate your way through fields of corn as far as the eye can see at a corn maze close to Boston. . Here are some ideas:

• Hanson’s Farms in Framingham
• Marini Farm in Ipswich
• Connors Farm in Danvers
• Sauchuk’s Corn Maze and Pumpkin Patch in Plympton
• Davis Mega Maze in Sterling

See the rest of the best corn mazes in Boston here!

9. Cheer on the Head of the Charles athletes

The Head of the Charles regatta returns October 20 this year. It’s a fun spectacle to cheer on the rowers from these five iconic HOCR viewing spots .

10. Go on a beautifully haunting hike through an abandoned ghost town

A spookier alternative to the classic autumn nature walk is exploring one of Massachusetts’ ghost towns. As our state is home to some of the first settlements in the United States, it’s no surprise that there are plenty of ghost towns around. Whether the original inhabitants abandoned the villages over decades or were forced to leave, there’s plenty of interesting history remaining for you to explore on a hike through ages past.

Check out the eerie magnificence of these towns:

• Quabbin Reservoir Towns
• Whitewash Village

View our full itinerary of Massachusetts ghost towns for a solidarity staycation.

11. Go glamping in the great outdoors

Fall weather can be unpredictable, but you can bet that a glamping experience is sure to be a comfortable getaway in nature this fall.  Glamping (glamorous camping!) provides all the beautiful scenery of the outdoors without sacrificing modern amenities. Luckily there are tons of glampsites around New England such as:

• Getaway in Epson, New Hampshire
• Normandy Farms in Foxborough, Massachusetts
• Maine Forest Yurts in Durham, Maine
• Tops’l Farm in Waldoboro, Maine
• Sandy Pines Campground in Kennebunkport, Maine
• Huttopia White Mountains in Albany, New Hampshire
• Autocamp in Cape Cod

While some require long car rides away from the city, the trek will absolutely be worth it. Check out our top picks for glamping outside of Boston for a lovely fall getaway.

12. Thrift shop for some seriously spooky Halloween costumes

Want to assemble a perfectly spooky Halloween fit? Look no further than your local thrift stores—thrifting is one of the best options to shop for Halloween costumes without breaking the bank, and Boston has no shortage of super-cool thrift shops where you can browse around. Our list of 9 Boston thrift stores includes boutiques and chains of all price ranges and styles, but no matter where you go, you’ll be certain to leave with a Halloween costume that’s completely unique.

13. Try out a new restaurant

There’s a plethora of new spots opening in Boston this fall. One of the most anticipated is the return of Eastern Standard ! It’ll open alongside 3 brand-new spots that promise delicious foods in lovely settings that will whisk you away from Boston into a flavorful world of gourmet innovation!

14. Or revisit a classic: the Apple Cider doughnut

It’s that time of year when local orchards and bakeries start serving those steaming hot, cinnamon-dusted delicacies we call apple cider donuts . When you’re craving a fresh-baked doughnut, you don’t have to travel too far to satisfy your cravings. Check out our list of the best places in in the city to get one (or a dozen), including:

• Blackbird Doughnuts
• Kane’s Donuts
• Wilson Farm
• Union Square Doughnuts
• Volante Farms

15. Catch legendary Oscar-winning Costume Designer, Ruth E. Carter at the Coolidge

View this post on Instagram A post shared by Ruth E. Carter (@therealruthecarter)

The Coolidge Corner Theatre will honor Academy Award winner, Ruth E. Carter with The Coolidge Award! The Springfield native designed costumes for  Black Panther, School Daze, Black Dynamite, and  Selma  to name a few! Celebrate with Carter and The Coolidge on October 15 at 6 PM! Tickets required .

16. Head out to the Flannel Jam fall music festival

View this post on Instagram A post shared by LEVITATE (@levitatebrand)

Old Crow, Medicine Show, Chadwick Stokes & The Pintos, Ali McGuirk and others will ring in the fall with a cozy, comfy music fest. The 2-day festival will take place in Marshfield and on Nantucket. “One percent of each ticket sold will be contributed to the Levitate Foundation, a non-profit whose mission is to cultivate vibrant communities by creating and conserving access to music, art and the outdoors.” Find the New England Flannel Jam October 8-9.

17. Get salty with the New Bedford Whaling Museum

There are many upcoming events and exhibits this month at the museum:

• All month long check out a 3D screening of  Blue Whales: Return of the Giants  and learn about the magnificent blue whale
• October 5 at 6 PM: Gather at a seaweed roundtable to study works dedicated to the slimy powerful kale of the sea
• October 19 at 6 PM: Explore the seafaring collections of the New York Yacht Club and enjoy a reception with fellow sea-savvy folk

18. Check out the Blue Shark installation at Franklin Park

In partnership with the Emerald Necklace Conservancy and Franklin Park Zoo, “Blue Shark Garden” by Aquinnah Wampanoag artist and marine scientist Elizabeth James-Perry debuts at Franklin Park now through November 2024.

19. Check out the free  Play it by Fear  spooky season concert

Enjoy live musical scores of spooky classics like Ghostbusters, The Twilight Zone, Stranger Things, and The Addams Family , along with scores from beloved, festive family classics like The Nightmare Before Christmas and Harry Potter.  Find it Tuesday, October 3 from 6-8 PM at The Rocks. And reserve your free admission online .

111 Harbor Way, Boston, MA 02210

20. Get inspired at the Chinatown Arts Festival

Now through October 14 explore the colors of Boston’s Chinatown. The rich artistic history of old and new is on display with 6 bold window murals, on bright display throughout the neighborhood!

Murals on display throughout Chinatown by artists include:

– “What Makes a Community Thrive” by BCNC Youth Center, 38 Ash Street

– “A Communal Blend” by Jennifer Duan at APM Coffee, 99 Kneeland Street

– “Unity” by Jinyi Duan at Crave Chinatown, 75 Kneeland Street

– “Welcoming Dishes” by Yuan-yuan Wang at WakuWaku, 2 Tyler Street

– “We Protect Each Other” by Yixuan Zeng at Q Restaurant, 660 Washington Street

– “Let’s Eat” by Jialu Zou at Happy Lamb Hotpot Boston, 693 Washington Street

21. Voyage to Grenada with the opening of ZaZiBar

Nestled in Boston Seaport is a new flavor profile you need to explore. ZaZiBar, a traditional Caribbean Asian restaurant brings the flavors of “The Spice Island” to the district. Spearheaded by Chef Olrie Roberts, guests can enjoy everything from Jerk Chicken to savory “bubble waffles.” Join ZaZiBar for its grand opening on October 10!

22. Make strides against breast cancer with the American Cancer Society

View this post on Instagram A post shared by Mike (@thlucky)

October is Breast Cancer Awareness Month. On October 1 at the Hatch Shell will be the 31st annual Making Strides Against Breast Cancer walk, where over 3,000 survivors, thrivers, and caregivers will dress in pink and parade around the Esplanade to honor those who are no longer here to walk. All month long there will be events to raise awareness honor survivors and encourage women to learn about early detection.

23. Wake up with a Pumpkin Spice Cold Brew from Blank Street

It’s pumpkin spice latte season, but let’s be real, most New Englanders are going to have the iced coffee or cold brew version- even as the temps dip. Blank Street released its Shaken Pumpkin Spice Cold Brew just in time!

The mix of pumpkin pie spice, cold brew, and milk taste like a crisp fall morning in a cup! Fun fact, unched the latest edition of its innovative and delicious Cold Brew Menu: The Shaken Pumpkin Spice Cold Brew from Blank Street sells 3x more than the regular Blank Street Pumpkin Spice Latte!

TYPE IN YOUR SEARCH AND PRESS ENTER

10 Best Road Trips to Take in Massachusetts

A laid-back road trip along Massachusetts' renowned highways offers travelers a unique opportunity to discover some of the country's most diverse and picturesque natural landscapes. From the sandy shores hugging Cape Cod in the east to the dense forests synonymous with the Berkshires in the west, it is a journey with a mixed bag of delightful surprises.

Between the start-off point and the destination, cute little towns, beautiful state parks, and roadside attractions present road-trippers with a glimpse of the state's historical heritage, cultural outlook, and natural splendor for a wholesome experience. Whether you are embarking on a solo trip or journeying with friends and family, these are some of the best road trips to take in Massachusetts.

Connecticut River Byway (39 miles / 63 km)

The scenic Connecticut River Byways stretches 39 miles (63 km) from north to south along the fertile course of the Connecticut River Valley. It is an exciting journey that exposes travelers to early American history as it passes through several historic villages dating back to Colonial times. Boasting several recognized historical sites and monuments along the route, there is no shortage of roadside entertainment to fuel your excitement. Some notable highlights to watch out for include the Connecticut River Greenway State Park, which offers 1,000 acres of hiking trails, waterfront vistas, and wildlife-watching opportunities.

The road also traverses the town of Deerfield, where the iconic Historic Deerfield Living History Museum profiles the colorful past of the Connecticut River Valley. In addition to the different sites, drivers can abandon their vehicles to exercise their legs while soaking up rich outdoor scenery.

Mohawk Trail Scenic Byway (69 miles / 111 km)

This beautiful roadway opened in 1914 and became a sought-after route for adventure lovers looking to discover the beauty of rural Massachusetts . The Mohawk Trail Scenic Byway stretches 69 beautiful miles (111 km) and links dramatic vistas, historic towns, and scenic hiking trails for an unforgettable escapade. The trip exposes bustling art communities showcasing rich local heritage. As it meanders through Williamstown, you can take a break to explore intricate creations inside the Williams College Museum of Art.

The journey also crisscrosses several rivers, allowing access to fun adventures like rafting and kayaking on the Deerfield and Millers Rivers. Meanwhile, hiking enthusiasts will gladly take on the Mahican-Mohawk Trail to test their mettle.

Mount Greylock Scenic Byway (16 miles / 26 km)

Discover the beauty of the Mount Greylock State Reservation along this 16-mile (26 km) climbing path in the Berkshire Mountains. The route's high altitude delivers stunning views of Massachusetts backcountry gems. It comes to its own in fall, with the changing foliage transforming the environment into a colorful natural wonder. Travelers following the parkway can access 70 miles (112 km) of nature trails that accommodate hikers, bikers, and bird-watchers, highlighted by a section of the Appalachian Trail .

The Bradley Farm Trail Loop is one of the most popular hikes for tourists looking to explore the thick wilderness surroundings. Dozens of vantage points encourage road-trippers to pause momentarily and take in the stunning scenery from above.

Historic Route 6A (62 miles / 100 km)

This scenic road along Cape Cod is also called the Old King's Highway. It cuts through a wealth of timeless historic sites, making it one of the best road trips to take in Massachusetts. The highway spans 62 miles (100 km) between Bourne and Orleans and traverses a combination of preserved farmland, salt marshes, and coastline. Driving along is a chance to witness centuries-old architectural styles in historic homes, restored inns, and ancient churches. Be sure to check the Old King's Highway Historic District of Barnstable, which houses over 500 ancient buildings and is listed on the National Register of Historic Places.

Other than history, alternative activities include walking on sandy beaches. Another exciting consideration is stopping by the beautiful Cape Cod Organic Farm to shop for fresh vegetables and organic meat.

Jacob's Ladder Scenic Byway (35 miles / 56 km)

This beautiful pathway is considered the ideal option for travelers visiting western Massachusetts. It sprawls approximately 35 miles (56 km) and crosses several towns along the foothills of the Berkshire Mountains. These include Lee, Becket, Huntington, Chester, and Russel, which serve as worthwhile stops with interesting local attractions during your trip. Jacob's Ladder Scenic Byway delights with well-preserved historical living history and a taste of unique New England culture.

Cultural attractions worth checking out feature the popular Jacob's Pillow Dance Festival, scheduled for August in the historic community of Becket. Furthermore, consider pausing the journey in Lee to admire 19th-century architecture and spend quality time shopping cheaply at the Lee Center.

Essex Coastal Scenic Byway (90 miles / 145 km)

Explore historic seaports, ancient villages, and Colonial farms when traveling along this extensive roadway along Massachusetts North Shore. The Essex Coastal Scenic Byway stretches approximately 90 miles (145 km) and winds past several beautiful communities with exciting legacies, including Gloucester and Newburyport. Each stop has something to offer tourists traveling the byway. For instance, Ipswich harbors a delightful coastal atmosphere flanked by a collection of First Period dwellings providing a window to the 17th and 18th centuries. Meanwhile, Newburyport delights with its shipbuilding heritage and distinct Federal-era architecture.

Also, Essex has pleasant antique shops where you can hunt for vintage souvenirs. Those who appreciate Mother Nature's beauty can discover a thriving ecosystem across the Parker River National Wildlife Refuge.

Battle Road Scenic Byway (15 miles / 24 km)

This historic pathway follows the route used by the British regulars in the lead-up to the American Revolution. It extends approximately 15 miles (24 km), plying through the quiet towns of Lincoln, Lexington, and Concord . While the journey is relatively short, multiple points of interest along the way allow you to prolong the experience while making it fun and memorable. Exploring the route offers a fresh perspective on the American Revolution by exposing users to literary and technological implications associated with the landmark event.

Noteworthy highlights that add to the experience on the road include Lexington Battle Green, a landmark conflict location that altered colonists' relationship with the British government. The route also traverses a portion of the sprawling Minute Man National Historical Park.

Central Hills Loop (57 miles / 92 km)

This remarkable 57-mile (92 km) journey takes tourists through several beautiful towns in central Massachusetts, each with unique natural scenery and points of interest. Possible stops in your itinerary are New Salem, Ware, Hardwick, and Pelham. While the Central Hills Loop is accessible throughout the year, fall is the best season for this trip as the foliage changes color. Besides the alluring greenery, you can stop at different overlooks to catch glimpses of stunning rock formations.

As you start, pass by the New Salem Preserves & Heritage Cider and sample delicious apples from the region and well-prepared doughnuts to stock up for the journey ahead. Upon reaching Hardwick, you will want to pull over to the curb and enjoy the cozy atmosphere of its historic covered bridge.

Boston to Plymouth (40 miles / 64 km)

Boston makes for an idyllic jump-off base for visitors planning to explore the state on an exciting road trip. The journey from Beantown to Plymouth lasts about an hour and covers 40 miles (64 km), delivering a mix of historical and urban attractions as you move along. While you will not run out of points of interest worthy of a stopover, the Plimoth Patuxet Museums (otherwise known as the Mayflower Museum) is an enticing prospect, presenting an opportunity to familiarize yourself with historic immigrant crossings.

Once in Plymouth, consider going for a captivating whale-watching excursion off the Atlantic coast, with a chance for rare encounters with humpback and pilot whales. Alternatively, you can visit Stellwagen Bank Marine Sanctuary to admire its cute sea creatures.

Lexington to Concord (7 miles / 11 km)

This short trip between these two iconic Massachusetts towns is perfect for those who do not have much time to spend on the road. It takes about 15 minutes between Lexington and Concord, and road trip fans get a front-seat pass to the inner details of the American Revolutionary War when driving along the 7-mile (11 km) highway. The major highlight here is the Minute Man National Historical Park, which provides a glimpse into the landmark conflict and several factors that led to its occurrence.

The site hosts several battlefields and historic structures, allowing you to relive the famous dispute. Although there are not many attractions on the road, the trip's historical significance makes it a popular option when your time is limited. The route also passes along the Louisa May Alcott’s Orchard House and Concord Museum for endless exhibits into the past.

Final Thoughts

Whether you seek to experience scenic coastal views, historic small towns, or bustling urban attractions, the Bay State delivers memorable backroad adventures. From Cape Cod to the Berkshires, each region uncovered along these beautiful road trips to take in Massachusetts immerses travelers in the diverse charms this New England jewel offers. Explore beaches, forests, museums, charming ports, and more without missing the experiences that make Massachusetts a top destination. Planning a variety of loop trips for the year guarantees pleasant discoveries around every bend in the road.

More in Places

Nevada's Best Small Towns For A Weekend Escape

8 Most Historic Small Towns to Visit in Oregon

7 Underrated Small Towns to Explore in North Dakota

7 Oldest Founded Small Towns to Visit in the Northern United States

6 Delightful Towns to Visit in The Poconos

9 Offbeat Towns to Visit in Western Australia

8 Oldest Founded Florida Towns to Visit in 2024

9 Most Historic Small Towns To Visit In Indiana

• Weather App
• Interactive Radar
• 7 Day Forecast
• Hour by Hour
• Current Temperatures
• Closings & Delays
• Report School or Business Closing
• School administrators: Create a closings account
• Watch Live News
• Breaking Stream
• The $pend $mart Stream
• Law & Crime
• Curiosity NOW
• Share Your Photos and Videos
• Karen Read Murder Trial
• 25 Investigates
• New England's Unsolved
• Boston Bruins
• Boston Celtics
• Boston Red Sox
• New England Patriots
• Zip Trips Market Place
• Furever Friday
• Steals and Deals
• Submit a news tip
• Advertise with Us
• TV & Stream Schedule
• Work at Boston 25 (Opens in new window)
• Visitor Agreement
• Privacy Policy
• Around Town
• Stuff the Bus

Boston 25 Now

Feeling like fall!

COOLER COUPLE OF DAYS

We are waking up to some clouds this morning, a spot shower is possible for the morning drive, but most stay dry. You’ll notice a big change in the temperature and humidity today, highs will struggle to reach the low 70s in some spots and it will feel much more comfortable. There will be a few clouds bubbling up today, but plan on some sunshine too. An upper level low pressure system will bring the risk for an isolated shower or storm this afternoon, but there is a greater potential Wednesday afternoon. The fall-like feel will continue through the end of the week with wake-up temperatures in the 50s and highs in the low 70s.

WEEKEND IN VIEW

The weekend is looking fantastic! Plan on plenty of sunshine Friday through Sunday, it will be warmer with highs in the mid 80s and a touch more humidity. It will stay dry for any outdoor plans this weekend, rain chances increase Monday with an approaching front.

© 2019 Cox Media Group

‘Can’t make sense of it’: Residents rattled after incident at North Andover home leaves 2 dead

JetBlue announces 5-day sale with flights out of Boston for as low as $39

‘Emptied his bladder on me’: Woman urinated on by ex-NFL player describes ‘nasty’ in-air incident

Two dead following ‘isolated incident’ at North Andover home, DA says

Duck boat rescues baby boy who fell into Charles River, dad who jumped in after him

6 Ways to Get Around Boston: A Guide to Efficient Transportation

If you are visiting and need to get around Boston, the public transportation system is the best way option.

A car rental may be tempting, but the only time it’s worth driving is if you’re heading to a destination that is not easily accessible by public transportation.

How to Get Around Boston

As a management consultant, I worked in the Boston area for a year and always had a rental car which was funded by the firm.

When I rented a car in Boston, I found that not only can driving be a nightmare, but parking is also nearly impossible and comes at a premium.

As with most larger cities, I recommend that you avoid being on the road during traffic hours as much as possible because believe it or not, it’s much easier to drive and find parking in New York City than in Boston.

On a more recent trip to Boston, it was still easy to get around Boston using the city’s efficient public transportation system. However, we didn’t need transportation for every part of town, and we were able to visit the most popular areas of Boston on foot.

The city is very walkable. When visiting the historic district and downtown zones, it’s best to travel on foot (and don’t forget the strollers for the little ones).

However, just note that historic streets are cobbled and may be difficult to navigate with wheels.

Now get ready to take some great photos in Boston , here’s a roundup of the best ways to get around town.

The Boston T

Boston has an incredibly good public transit system called the MBTA (Massachusetts Bay Transportation Authority), or to locals, the “T” and it is the most popular way to get around Boston.

I found the maps easy to read and we used them to get to all the places on our itinerary. It is the best mode of transportation in Boston, the suburban towns, and smaller cities within Eastern Massachusetts.

The “T” has five color-coded branches that run above and below ground. There is also a map at every station and on most of the individual cars and ticket kiosks.

Daily or weekly passes are also available. You just need to decide if you need a CharlieCard (a plastic reusable card) or a CharlieTicket (a paper ticket).

You can also pay cash; they are accepted on buses and trolleys with fare boxes. 

And there is good news! Unlike cities like London, you can get around in Boston with no extra fee for peak periods. All fares are the same no matter what time of day or day of the week that you travel.

You can also pay for more than one person if you have a CharlieCard (but it doesn’t apply to CharlieTickets), so there is no need to purchase multiple cards.

Just tap your crew through the turnstile and keep it moving! Activation for the CharlieCard begins on first use. 

Cost & Service:

• One-way – $2.40, transfers included
• Day pass – $12.75 for unlimited rides in 24 hours
• Weekly pass – $22.50
• Service – 5 AM to 12Am and later on weekends

I imagine traveling on the “T” has become a challenge over the years, just as it has in Chicago due to crowding and undesirable behaviors. Just keep your wits about you, secure your belongings, and avoid peak travel periods (before and after business hours).

Many cities are making an effort to be more eco-friendly, and Boston is no exception.

With the development of new street lanes and paths, biking has become a safer and more economical mode of transportation.

It’s a healthy way to get around Boston and bikes make it easy to navigate the street and sidewalks.

The bike-sharing program is called BlueBikes and with the app, you can manage membership and rentals.

The plans are created to benefit frequent riders so if you sign up and cancel the membership, you are still responsible for the remaining balance.

Some companies, like Urban AdvenTours, rent bikes on an hourly or daily plan. Renting a bike is a great way to see the city, get exercise, and create your own sightseeing agenda.

If the weather is great, it will be easy to get around Boston as a first-time visitor or take a ride along the harbor.

The Boston Trolley

We were huge fans of the HopOn-HopOff when our stay is short, and we want to see as much as possible in a short amount of time. We rode this tourist bus and saw quite a few famous sites in half a day, which allowed us to explore other parts of the city during a long weekend.

Tickets can be obtained at the booths and select hotel concierges.

The Green line is the most traveled route and travels through the Historic Downtown, Beacon Hill, Back Bay, North End, and Seaport districts. The first HoHo stop begins at Faneuil Hall and tours start daily at 9:00 AM. The last tour leaves at 5:00 PM during peak season (4:00 PM, non-peak).

Buses are inexpensive to get around Boston, but it is also slower than the “T”. However, the savings are hardly worth it unless you are traveling a short distance.

Cost: $1.70, transfer included

There are two harbor ferry routes that travel in the harbor and it’s a great way to see the city from a different perspective and get around Boston harbors.

The Charlestown Inner Harbor Ferry runs from Boston to Charlestown, and the Hingham/Hull Commuter Ferry travels between Boston, Logan International Airport, Hingham, and Hull.

Prices are affordable and it would be a nice way to spend time on the harbor at a low price point if the trip didn’t finish in the blink of an eye.

Cost: $4 – $10, one way

Commuter Trains

A commuter train is a great option to get around Boston or outside the city, for taking a day trip to Providence, Rhode Island, or accessing nearby suburbs. Prices vary depending on the start and end zone.

Compared to the Peter Pan bus, a trip to Providence will cost about $16.00 for a one-way fare and both methods are close in duration for traveling from city to city.

The commuter weekend ticket is valid on Saturdays and Sundays for unlimited travel between zones and only costs $10. That’s a nice deal for a one-day getaway out of Boston.

Cost: $2.40 – $13.25 one way

Traveling Outside of Boston

How to get from boston logon airport to downtown boston.

Depending on the proximity of your destination, you’ll take the Silver Line (1, 2, or 3) and transfer it to one or more of the color-coded “T” lines. Transfers are free.

The cost of a one-way fare on the Silver line is the same as the color-coded lines. Line 3 will take you to Chelsea or to the Blue Line which takes you to historic downtown Boston. Lines 1 and 2 will transport you near to the Seaport District or Chinatown.

We found this mode of transportation very simple to understand and follow when we were leaving Boston. Just follow the same steps in reverse.

Cost: $2.40, one-way

If you are up for a one-day adventure elsewhere like a tour of the Newport Mansions, here are some ways to get to other common destinations around Boston.

How to Get from Boston to Cambridge

We took the “T” that connects to the Red line and exited at either Harvard station.  You can also exit at Central Station.

We wanted to visit outside of Boston to see the Harvard University Campus and take photos. It is a beautiful neighborhood, and the ride was about 30 minutes from the city center.

How to Get from Boston to New York City 

A bus from Boston to New York takes about five hours on a good day with a bit of traffic. We found tickets for $7 per person with Megabus.

Another bus line is Peter Pan but the tickets tend to be slightly more expensive but under $60 one-way. A quick trip by train leaves from South Station with service via Amtrak Acela and the lowest price you will find is in the $30 range.

Driving is about 4 hours, more so with traffic. The drive from Boston to tour New York City is an easy 220-mile stretch. The only other costs you will aside from gas are tolls.

Flights are in the $100 range but consider the time spent getting to the airport, snaking the TSA line, and potential flight delays.

Cost: Varies

How to Get from Boston to Rhode Island

We caught the Peter Pan bus from Boston South Station to Rhode Island Convention Center stop. The ride was less than an hour. The bus was quite comfortable and with air-conditioning. At the time, the ticket cost us about $30 per person round trip.

Since it was only 25% full, we had a lot of space to spread out and we loved that the bus was equipped with charging stations at every seat.

How to Get from Boston to Martha’s Vineyard

While you can drive a car in Martha’s Vineyard, the only way to transport the vehicle is via the Steamship Transport Authority.

So, you’ll need to get to one of two ports: Woods Hole in Falmouth, MA or Hyannis in Barnstable, MA (Cape Cod). Assuming you don’t have a car, the easiest way is to leave from Boston Logan Airport and a Peter Pan bus to Woods Hole terminal.

Then walk about 10 minutes to the port. The trip is 2 to 2.5 hours in duration. From Boston Logan, you can also take the Plymouth & Brockton bus to the port, the savings is $2 or $3 dollars.

Cost: $30 range

Final Thoughts on How to Get Around in Boston

I walked a lot in Boston and my feet were hurting at the end of the day, but I easily get 30,000 steps logged on any given vacation day.

Overall, Boston has a great public transportation system that is very comprehensive. Like Chicago’s transportation system and New York, the system is expansive and makes it easy to explore beyond the familiar tourism spots.

We used it to visit South Seaport, the Isabella Gardner Museum, to get to the airport, and to take a 2-day side trip to Rhode Island.

On my next visit to Boston, I would use public transportation to get around Boston in a heartbeat.

If you have a car, the New England area is a lovely drive especially in the fall when the jewel-colored leaves are on display.

Happy trails!