Planning a road trip to Massachusetts? Save some time to explore some of the many epic day trips from Boston, MA! Within a few hours’ drive from New England’s largest city, we’ve experienced everything from cute historic towns to beautiful beaches.
As much as we love Boston, sometimes the city’s hustle and bustle can be too much. Our New England adventures have taken us to historic villages and seaside towns around Cape Cod, outdoor gems like Halibut Point State Park, and beautiful cities like Providence, RI, and Hartford, CT.
Got extra time to explore on your Bean Town visit? Venture outside the city limits to experience New England’s magic with our guide to some of our favorite Boston side trips…
Cape Cod, MA
In our opinion, Cape Cod is the quintessential New England beach experience. Located southeast of Boston, the long crescent-shaped stretch of beautiful beaches here are lovely places to escape the city, soak up the sun, and take a dip in the Atlantic Ocean.
A road trip from Boston to Cape Cod takes about an hour an a half, making it, in our experience, the perfect day trip!
Travelers who enjoy history will love exploring the towns and villages of Cape Cod. We’d suggest starting with Provincetown, the site of the Mayflower’s landing in 1620, and historic attractions like the Race Point Lighthouse. It’s the peninsula’s liviliest town, and has, in our opinion, the area’s tastiest culinary scene.
We’re also fans of Barnstable, the largest town on the peninsula. Our suggestion would be to explore is the historic Barnstable Village, which is one of our favorite tourist attractions in Cape Cod. We love the classic New England feel of this historic town center!
Nature lovers can explore parks like Monomoy National Wildlife Refuge, the Cape Cod National Seashore, and Nickerson State Park.
We’ve also discovered plenty of world-class museums around Cape Cod specializing in everything from classic cars to fine art. A few of our favorites include the Sandwich Glass Museum in Sandwich, the Cape Cod Museum of Art in Dennis, and the Whydah Pirate Museum in Yarmouth.
Venture to traditional lighthouses on the coast or hop on a ferry to the gorgeous resort towns of Martha’s Vineyard. Wrap up the day with delicious seafood before heading back to Boston.
Newport, RI
Take in the luxurious Gilded Age mansions of New York City’s elite in Newport, Rhode Island. Once the summer playground of the mega-wealthy tycoons, Newport remains a gorgeous destination year-round—and its one of our favorites historic cities to visit on any New England road trip!
We love wandering the streets of Newport to uncover its elaborate houses, demonstrating the finest 19th- and 20th-century architecture in New England. Historic preservationists have restored many of the palace-like homes to their original glory.
Visitors can tour many of the properties and imagine what it might have been like for the mega-wealthy who once lived in the monstrous homes.
The Breakers—a glitzy Italian Renaissance-style mansion with 70 rooms and a three-story dining room—will make visitors feel as though they have stepped back in time. Marble House is also worth a visit, with its gorgeous salon and luxurious Chinese Tea House.
After touring the historic mansions, we’d recommend taking a hike along the iconic Cliff Walk path to see them from the shore. On our quick Newport visit from Boston, it was one of our favorite moments!
Concord, MA
History buffs will rejoice on a visit to Concord, MA, the location of the first battle of the American Revolution. Just outside of Boston, the town of Concord is rich in military history and beautiful architecture. And at less 35 minutes (without traffic), it’s one of the quickest and easiest side trips we’ve found!
Besides its Revolutionary War history, we discovered that many brilliant 19th-century minds once called Concord, MA, home. Ralph Waldo Emerson, Henry David Thoreau, and Louisa May Alcott are just a few famed thinkers and writers who we learned lived and worked in Concord during the transcendentalist period of American Literature.
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We can spot the imprint off these writers all over town. A few of our recommended spots to check out include Louisa May Alcott’s Orchard House, The Old Manse, where both Ralph Waldo Emerson and Nathaniel Hawthorne lived, and The Wayside Home of Authors.
And our favorite stop? The famous Walden Pond is a natural retreat where Thoreau built a cabin and lived, contemplating the meaning of life, spirituality, and nature. (And that inspired Walden; or, Life in the Woods, one of Thoreau’s most important and famous works!)
We think Walden Pond is a magical place full of natural beauty and worth a day trip all on its own. Walking in the footsteps of some of America’s most brilliant and creative minds might inspire you, too!
Lexington, MA
On April 19, 1775, the sound of gunfire echoed from what is now the Lexington Green, also known as Battle Green. Those shots would mark the start of America’s War for Independence and forever cemented Lexington, MA, in American history.
If you ask us, there’s hardly a more ideal day trip for history buffs and American Revolution enthusiasts than Lexington. Located only 25 minutes from Boston, it’s an excellent option for a full or half-day trip.
Ambitious day-trippers can even combine a trip to both Lexington and Concord for a full day of historic fun.
Gorgeous parks, sculptures, and historical attractions are just a few elements that, in our opinion, make the beautiful town of Lexington well worth a side trip during your Boston vacation.
Naturally, we’d recommend starting with the Lexington Battle Green. Hop onto a walking tour to enjoy a historical reenactment from locals dressed up in colonial-era garb.
Guides will walk you past several historic attractions here, including the Revolutionary War Monument, a granite obelisk erected in 1799. We’ll also get to pay respects to American soldiers who helped to win America’s independence at the Old Burying Ground.
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One of our favorite activities here is to visit the immaculately restored 1710 Buckman Tavern, where the militia used to come together to strategize. Or, if you haven’t got your fill, we’d suggest taking a walk through Minute Man National Historic Park to immerse yourself in Revolutionary War History.
Rockport, MA
When we’re looking for a classic New England seaside retreat with plenty of nature without venturing too far from Boston, we head straight to Rockport, MA.
Located only an hour outside of Boston, Rockport, Massachusetts, is an idyllic seaside town that makes for an excellent day trip. We always love exploring the rocky landscape of Cape Ann on a rigorous hike or relaxing and enjoying nature at Halibut Point State Park.
Visitors can try their hand at recreational activities such as swimming, sailing, diving, or kayaking. Rockport is packed with rugged cliffs and a beautiful village for nature lovers and outdoor enthusiasts. Local outdoor outfitters offer stand-up paddleboarding tours, seal tours, and island tours.
Even with all of the exciting activities, we wouldn’t blame you for choosing to spend the whole day relaxing on the pristine beaches and enjoying a picnic lunch. The beaches closer to the town center—Front Beach and Old Garden Beach—are good options if you don’t want to stray far.
If you’re visiting on a Saturday, don’t miss a trip to the Rockport Farmers Market, which is open from 8 am to noon. We think it’s the perfect place to find tasty local delicacies to pack in your picnic basket.
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In addition to plenty of nature time, we love Rockport’s pretty downtown area. It’s got plenty of romantic dining options for couples to enjoy during their vacation. Some of our recommended restaurants in the area include Fleur Cuisine Harborside, Feather & Wedge, and Brackett’s Oceanview Restaurant.
We don’t think there’s a better way to wrap up an unforgettable day trip than to drink wine at a waterfront restaurant and gaze out over the ocean!
Newburyport, MA
If you’re a fan of historic architecture, we’d suggest adding the coastal town of Newburyport, MA, to your trip plans. Only 35 minutes from Boston, the city of Newburyport has ten historic neighborhoods for travelers to enjoy.
The entire downtown area is full of well-preserved historical buildings. Explore the Market Square Historic District, admiring the Federalist-era architecture along Water Street, State Street, and Liberty Street. Or enjoy a show at one of the many performance venues—like the Firehouse Center—before returning to Boston.
Travelers who enjoy getting outside in nature will love walking along the boardwalks through the sand dunes and the woodland paths along the beach at Parker River National Wildlife Refuge on Plum Island.
Portsmouth, NH
If you love museums, breweries, and historic homes, we think a day trip to Portsmouth, New Hampshire, might just be up your alley. Portsmouth is the oldest city in New Hampshire, dating all the way back to 1623.
We love strolling around this historic town, full of attractive 17th- and 18th-century buildings. Among them are several historic homes that visitors can tour, including Warner House.
While walking around town, we stumbled upon some great green spaces. Our favorite was Prescott Park, a 10-acre seaside public park that showcases gorgeous colors from spring until fall with its beautiful flower gardens and weeping trees.
Visiting during the warmer months? Prescott Park hosts a variety of fun outdoor concerts, events, and arts festivals. From the Liberty Pole, there are free park tours at 11:00 am and 1:00 pm on Fridays during the summer.
Perhaps even better than all its historical attractions is its lively bar and restaurant scene. Before leaving, we’d recommend pulling up a seat to enjoy some classic New England seafood at a harborside restaurant like River House or Surf Portsmouth.
Providence, RI
Art lovers and creative types will love throwing in a visit to Providence, RI. Rhode Island’s largest city is about an hour from Boston, and we think it’s a fun side trip that’s perfect for exploring more of New England’s cultural highlights!
Let’s start with Providence’s hip downtown area. It’s a great stomping ground for travelers who like to keep it trendy. While wandering around, we’ve spotted plenty of murals that offer ample opportunities to snap the perfect photo to brighten up your Instagram feed.
Some of our favorite activities in Providence, RI, include visiting art museums, hiking, and shopping. If you love architecture as much as we do, you’ll appreciate the city’s unique buildings bedecked in Art Deco and Victorian styles.
Love whipping out the wallet on vacation? We’d highly recommend shopping until you drop at The Arcade, America’s first shopping mall, which has been around since 1828.
Of course, we don’t think any visit to Providence is complete without eating and drinking at the many tasty bars and restaurants. Slip into Hemenway’s Restaurant, one of the city’s most popular restaurants, for a taste of local seafood washed down with a selection from the extensive wine list.
Hartford, CT
Looking to check off another New England capital for your bucket list? Set aside time to explore Hartford, Connecticut. Just over a 90-minute drive from Boston, Connecticut’s capital always surprises us with its art, history, architecture, and literature!
We’re huge book lovers. So, obviously, our first stop in Hartford will always be the Mark Twain House and Museum. The famous American author’s home, now turned into an interesting museum, is, undoubtedly, one of our favorite tourist attractions in Hartford, CT.
The Mark Twain House features plenty of personal belongings and artifacts belonging to the author, including the original writing desk on which he wrote so many classics. We’ve seen a variety of cool events advertised at the museum throughout the year, ranging from Mark Twain-themed beer tastings to literary events.
For another historical gem in Hartford, we’d suggest sliding into the Harriet Beecher Stowe Center. Go inside her historic mansion, filled with authentic period-appropriate furniture, to learn more about the absolutist and author’s life and works, including her most famous book, Uncle Tom’s Cabin.
If you’re interested in fine arts, head straight to the Wadsworth Atheneum Museum of Art to browse its eclectic collection of 19th- and 20th-century American art.
Or, for travelers with kids in tow, we think the fun hands-on exhibits at the Connecticut Science Center would be a better choice to fill your Hartford visit.
Portland, ME
While it’s a little further afield than our other suggestions, we can’t help but recommend Portland, Maine, to round out your New England experience. The coastal city gets our nod for its fantastic shopping, exceptional seafood, and historic buildings.
Portland is a two-hour drive or train ride from Boston, and, in our opinion, this port city offers some of the tastiest seafood in New England! (You see, there’s always a method to our madness.)
We think the historic district of Old Port is the perfect place to start. Wandering along the picturesque cobblestone streets, you’ll discover a ton of great shopping options and a variety of restaurants and bars. Browse through the unique clothing boutiques, gourmet food stores, and gift shops while enjoying the classic New England coastal beauty.
Now for the really good stuff…
Foodies visiting Portland, ME, will love tasting various New England dishes like lobster rolls and clam chowder, and unique delicacies like potato donuts.
When we’re in Maine, we always find wonderful waterfront dining options. Seafood lovers who want to sample the catch of the day while gazing out at the harbor should check out seaside restaurants like Scales, Luke’s Lobster Portland Pier, or DiMillo’s On the Water.
We’d also be doing you a disservice to not recommend the succulent Maine lobster and crab rolls at The Highroller Lobster Co. on Exchange Street in Old Port; they’re simply divine!
