8 Best Weekend Getaways in Massachusetts
Rolling hills, picturesque small towns, historic places, acclaimed museums, and private beaches: This is Massachusetts away from its urban centers like Boston. In the Bay State, summer serves up ideal weekend getaway weather, and, as of the end of May the state will be almost fully open. Whether you want the Berkshires or the beach for your upcoming summer holidays, here are the best weekend getaways in Massachusetts.
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All products and listings featured on Condé Nast Traveler are independently selected by our editors. If you purchase something through our links, we may earn an affiliate commission.
GettyPlymouth
45 minutes from Boston
Visitors are welcome at the 401-year-old Plimouth Patuxet, the living museum dedicated to the 1620 arrival of the Pilgrims at nearby Plymouth Rock. At the settlement, actors revive traditions, clothing, and customs from the 1600s for an immersive experience. In downtown Plymouth, travelers can also walk through Brewster Gardens, a park that hugs the banks of Town Brook, the 1.5-mile long stream that provided the Pilgrims with their drinking water. Grab a seat outside for dinner at the Rye Tavern at The Pinehills, then retire to a spacious, well-appointed suite at the Mirbeau Inn & Spa (rooms from $280 per night).
GettyNewburyport
1 hour from Boston
Founded in 1764, this postcard-perfect coastal town on Massachusetts’ North Shore offers original Colonial and Federal architecture, as well as a wealth of American history: it’s home to the United States Coast Guard, and to William Lloyd Garrison’s abolitionist weekly Liberator Magazine. By day, beach it on Plum Island, Newburyport’s 11-mile-long barrier island that faces the Atlantic (Plum Island is part of the Parker River National Wildlife Refuge). By night, cruise the brick-paved downtown area, and stop in for dinner at the Paddle Inn, a surf-inspired restaurant popular among locals. The six-room Compass Rose Inn (rooms from $199 per night) offers working fireplaces in most rooms and a cupola with a water view.
GettyMarblehead
45 minutes from Boston
This waterfront enclave on Cape Ann is home to beaches, hiking trails, and historic properties. More than 300 of Marblehead’s homes date to the 17th and 18th centuries, and you can see them by parking at Bank Square and exploring the town on foot. Tour the Jeremiah Lee Mansion & Garden, a Georgian-style home built in 1768, and then head over to the Little Harbor Lobster Company—a century-old restaurant known for its local seafood that has shifted during COVID-19 to a curbside delivery and takeout model. Marblehead’s best accommodations can be found at The Harbor Light Inn (rooms from $199 per night), which, in addition to its 20 rooms, offers five full apartments and in-season swimming pool.
GettyLenox
2 hours 45 minutes from New York City
Author Edith Wharton made her home in Lenox, Massachusetts, at the turn of the 20th century (her estate, The Mount, is open for historic tours most days), and the natural beauty on which she capitalized persists today. Commune with nature at Miraval Berkshires (rooms from $1,568 per night), a 100-room all-inclusive wellness resort that opened—on over 350 acres of manicured woodland—in July 2020. Miraval offers equestrian activities, culinary classes, spa treatments, and yoga. Try your hand at the Red Tail Hawk ropes course, at which guests are clipped into a series of aerial obstacles high in the trees. Or, if you prefer to have your feet planted firmly on the ground, take the resort-led, three-hour-long Beartown Hike, in the nearby town of Monterey.
GettyConcord
35 minutes from Boston
This famed Revolutionary War city is known for more than just its battles. Walden Pond, where Henry David Thoreau sought solace from the world, is a kettle hole pond here that was formed by retreating glaciers. Visitors can swim, hike, and boat at Walden and, when restrictions ease, visit the Thoreau House Replica to see how the author lived. Built in 1885 and recently reopened to guests, the North Bridge Inn (rooms from $250 per night), with its six suites, is within walking distance to Concord’s Monument Square, and to restaurants like the critically acclaimed 80 Thoreau.
AlamyChilmark
3 hours from Boston, includes ferry
On the west side of Martha’s Vineyard, you’ll find the bucolic town of Chilmark, population 917. Lucy Vincent Beach is Chilmark’s crown jewel, but there’s plenty to do in this rural Vineyard outpost besides spreading out in the sand. Larsen’s Fish Market, a waterfront stalwart since 1969, serves fresh-shucked oysters on paper plates. Thursdays through Mondays, travelers can visit The Grey Barn, a farm and creamery founded in 2009 that sells raw milk, eggs, vegetables, certified organic meats, and a full line of cheeses. Woodlands and wetlands define the roughly 185-acre Wasoskim’s Rock Reservation, which is open for hiking, horseback-riding, mountain-biking, or, if you aren’t in the mood to be active, just picnicking. Retire to a beachy room or bungalow at the quaint Beach Plum Inn (rooms from $510 per night), also home to one of Martha’s Vineyard’s best restaurants, and only available to guests of the hotel.
GettyChatham
1 hour 30 minutes from Boston
Find Chatham, Massachusetts, on the southeastern tip of Cape Cod. The town’s Lighthouse Beach is frequently named one of the state’s most beautiful and offers a view of the 19th-century lighthouse here. The donations-only Chatham Railroad Museum, located inside an 1887 train depot, features a wood-sided red caboose built in 1910. No visit to Chatham would be complete without a meal at The Impudent Oyster, the four-decade-old ode to seafood (and to laid-back South Shore dining). To stay, book the Chatham Bay-facing Chatham Bars Inn (rooms from $535 per night), which has held court on the Cape since 1914.
GettyWilliamstown
3 hours from New York City
The place to stay in Williamstown is the 64-room Williams Inn (rooms from $249 per night). The hotel’s rustic comfort, paired with its prime real estate—it’s a short drive to MASS MoCA, one of the largest centers for contemporary visual art in the country—makes it a desirable stay in this rural northwest corner of the state. Through October, Williamstown’s Clark Art Institute is showing Claude & François-Xaviar Lalanne: Nature Transformed, the first American exhibit of these French sculptors in the past four decades. For a bite, seek out the local and seasonally minded Mezze Bistro + Bar (dinner is served four nights a week, with a takeout menu available five nights).
