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Portland, Maine
Photograph: Courtesy Visit MainePortland, Maine

The best day trips from Boston

Take a break from the city by heading to a historic Colonial town or beautiful seaside port

Written by
Linda Laban
Time Out Boston Staff

Given how intense life can often be in our humble metropolis, every Bostonian gets a little stir crazy now and then, especially during these times of social distancing and working from home. Fortunately, all one has to do is hit the road — or hop on a train, bus or ferry — to explore the many wonders of New England. The Hub’s main arteries (I-90, I-93 and I-95) give direct, easy access to Maine, New Hampshire, Connecticut, Rhode Island, western Mass, and even Vermont; this means locals have lots of enticing day trips to choose from at any time of the year. Once you’ve returned to the city, keep the fun going by checking out the best Boston attractions, best free things to do in Boston, and best museums in Boston.

RECOMMENDED: Full guide to the best things to do in Boston

Best day trips from Boston

Portland, ME
Photograph: Courtesy Visit Maine

1. Portland, ME

Maine's largest city—around a two hour drive north of Boston—attracts foodies from around the country. Wander the charming, hilly Old Port district, where every kind of boutique imaginable touts colorful wares and quaint pubs and dimly lit cocktail bars, like the excellent Blyth & Burrows, which combines the best in innovative mixology and pairs it with equally scrumptious small plates, are set along cobble stoned lanes. 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 lives up to the hype: Dine at Evo Kitchen + Bar for progressive twists on Mediterranean cooking, and Union, a vibrant local-centric foodie haunt in The Press Hotel, set in the former home of the Portland Press Herald, the state’s largest newspaper.

The Newport mansions of the Gilded Age still impress, and that’s what they were built to do. (If you have time for only one, check out The Breakers.) Near the International Tennis Hall of Fame, the Audrain Auto Museum houses a seasonally rotating display of impressive cars inside a gorgeous Art Deco building.

Take the Cliff Walk, which has stunning views over 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. Near the harbor, Bowen’s Wharf’s harbor buildings date back to the 1700s and today offer 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.


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), when militia engaged with British troops igniting the Revolutionary War. The 19th century Transcendentalist movement and its influential authors and thinkers—Ralph Waldo Emerson, Henry David Thoreau, and Bronson Alcott and his family—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.

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

Providence is a food lover’s dream. Why does this small capital city have so much kitchen talent? Nearby Johnson & Wales Universitys College of Culinary Arts is a major factor. Hemenway’s in downtown is the grand dame of area seafood restaurants; and Waterman Grille is a hidden jewel on the East Side near Brown University. Federal Hill, the city’s impressive Italian neighborhood, is loaded with Italian eateries and shops. Yoleni’s is a multi-purpose culinary concept with 40,000 square feet of Greek goodies.

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 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.


Salem is forever linked to its 1692 witch trials. Interested parties flock to the home of presiding Judge Corwin, which today is a museum known as The Witch House. Halloween’s a big thing here; so are new age and cult shops. On a cheerier 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. (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—nestled between the woods and the ocean, a ten minute drive from downtown, in Forest River Park—reenacts early 17th century colonial life. Eat like a local at Ledger or Bambolina, or nerd out with old school arcade games and pinball machines at Bit Bar, housed in the site of the Old Salem Jail.

Provincetown, MA
Photograph: Courtesy Creative Commons

6. Provincetown, MA

Creative, sassy P-town — only a 90-minute ferry ride from Boston — is an artsy LGBT hot spot; it’s got a great mix of galleries showing nautical scenes and nightclubs doing fun cabarets. 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 Lobster Pot is the biggest name in town for classic lobster rolls and fresh seafood treats from the sea. Climb the 252-ft. 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 the suave Sage Inn’s lounge and great seafood at Mac’s Fish House, which has crispy fish and chips and Happy Hour buck oysters. Explore the beautifully barren Outer Cape’s stretch of the Cape Cod National Seashore, including Truro’s picturesque Highland Light. (Truro is also home to the fun, fertile Truro Vineyards and South Hollow Spirits.)


The Newburyport Historic District, which encompasses most of the historic 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. (The Custom House Maritime Museum also unravels local history.) The beautiful Waterfront Park and boardwalk has regular concerts during warmer months.

Newburyport offers exceptional boutiques for browsing: crate diggers head to Dyno Records on Middle Street, and The Dragon’s Nest toy store on Market Square has something for kids of all ages. Catch a play or see a show at the Firehouse Center for the Arts; relax with excellent cocktails and fine pizzas at The Poynt; dine on classic seafood at Michael’s Harborside; or grass-fed beef and tasty veggie dishes at Superfine Foods. About a mile away, the Newburyport Brewing Company offers a friendly tap room and beer garden. Newburyport includes part of neighboring, sedate Plum Island, a barrier island overlooking salt marshes. Opt for a deck seat at sunset at the Plum Island Grille.

Ogunquit, ME
Photograph: Courtesy Visit Maine

8. Ogunquit, ME

Set on the breathtaking Maine coast, Ogunquit is a popular, classy beach town with a quiet ambiance, particularly in the cooler months when crowds disappear. But it is 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, a pleasant walk away, and get tickets to a show at the Ogunquit Playhouse, which notches up eight decades of professional theatre and summertime children’s productions, and is one of the last incubator “Straw Hat,” or summer stock, theaters.


Shipbuilders and fishermen made Gloucester prosperous; both industries still exist, but 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.

Catch a flick at the unique Cape Ann Cinema & Stage, which is furnished with vintage couches, recliners, armchairs, and coffee tables instead of regular cinema seats. Across narrow Main Street, savor straight-off-the boat seafood at the chic basement restaurant, Tonno. Or head to the Beauport Hotel, whose 1606 Restaurant has a great deck with ocean views, and a cozy fireplace for colder months. Next door to the hotel, Beauport Cruise Lines has seasonal jaunts around the harbor.

One aspect to a day trip in Lexington is that you can easily do it by bicycle along the Minuteman Bikeway, which begins in North Cambridge and runs right through leafy Lexington, some 15 miles northwest of Boston. This posh town is most famous for its historic Battle Green, where the bloody Battle of Lexington followed the 1775 skirmish at Concord, as patriotic Minute Men engaged the British Army on Lexington Common (thereafter known as the Battle Green). Many of the original homes flanking the battleground are preserved, including one 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 Cucina Campana + Bar from local chef Dante de Magistris, who traces his family’s roots with 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 Artistry on the Green restaurant is a modern pleasure involving artful, seasonal dishes.


Falmouth is nestled on the southwestern part of Cape Cod, 20 miles south of the Sagamore Bridge. Despite being lined with great beaches, cool boutiques, and relaxing spots to eat and drink, it's one of the Cape’s least touristy towns. Do breakfast or lunch like a local at The Pickle Jar, and the Bear in Boots gastropub has craft beers, great food, and fun events.

The Falmouth Museums on the Green brings Cape Cod in the 1700s 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 past lovely views of both the Vineyard Sound and Buzzard’s 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.

First stop: Bob’s Clam Hut, a sixty-year-old roadside diner with the best fried clams, sustainable local fish, and amazing milkshakes. Bob’s is adjacent to Kittery Premium Outlets, which has everything from discounted Calvin Klein wear to Lindt chocolate. Best 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, and a sake brewery, Blue Current Brewery.

The heart of Kittery Foreside, the downtown area, is Wallingford Square, which is dotted with all kinds of eateries including the sleek bistro Anneke Jans. Lil’s Café is set in a converted bank, where the old walk-in safe is now Vintage Vinyl, 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.


Just off I-90, Stockbridge is the gateway to the beautiful Berkshires, part of the Taconic Mountains. Main Street is wonderfully dominated by the venerable Red Lion Inn, a onetime frontier town tavern that still maintains a rousing bar, plus a casual eatery and a gorgeously original dining room with progressive locavore, seasonal food.

Nature and art dominate this 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, is a haven for music lovers. Nearby, take a guided tour of Edith Wharton’s home, The Mount, and learn why the woman behind the building and the stories is far more fascinating than either.

Visit Plymouth Rock and the stunning replica of the Mayflower in the harbor, and Pilgrim Hall, the oldest continuously operating public museum in the country. Nearby, Plimoth Plantation replicates the original Pilgrim village and doesn’t sugarcoat the early intersection of Europeans and Native Americans.

Return to the 21st century for a delicious cocktail at WaterFire Tavern at the John Carver Inn & Spa. Visit the Mayflower Brewery and  Independent Fermentations Brewery (which uses locally grown barley, wheat, and rye malts), or  Plymouth Bay Winery, which produces wine from locally-grown native grapes and berries. Don’t miss Eco Chic Gifts, which carries recycled, up-cycled, fair trade, organic, all-natural, and always chic stuff to ease your consumer conscience. Pair with some serious spa time at Mirbeau Inn & Spa, and add dinner in the hotel’s picturesque bistro overlooking gardens straight from a Monet painting.

Washington, CT
Photograph: Courtesy Mayflower Inn & Spa

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; Bee Brook Park is a pop-up park featuring environmental art by notable muralists.

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 TV program’s fictional Stars Hollow. Surrounded by colonial architecture, shop in unique boutiques and treat yourself to dinner (and a room, for a real spurge) at the historic, luxurious Mayflower Inn.

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