23 best weekend getaways from Boston

It’s only a little over an hour’s drive up to York, but it feels worlds away. This beach town packs in the best parts of a New England summer (sun, sand, and saltwater taffy, namely) without demanding a long haul. 

Eat at: Stones Throw, a bustling spot overlooking Long Sands Beach. Sample the spicy thai coconut mussels and herby falafel, then consider taking a canned cocktail to go. Make time to venture to nearby Ogunquit, too, for a meal at Northern Union. (And don’t leave without an order of the lobster deviled eggs.)

Stay at: The stunning new shoreside rooms at the Viewpoint Hotel offer something no other lodging in New England can: a postcard-perfect view of Nubble Lighthouse. The rooms are built into a Cape Neddick hillside facing the landmark, and feature floor-to-ceiling windows to maximize the setting. But if it’s a beachier weekend you’re after, settle into the The Nevada motel, the Viewpoint’s newly opened sister property.

Must do: You can’t visit York without a stop at the Goldenrod to watch saltwater taffy being stretched in the window—and to pull up a stool at the old-fashioned soda counter. (Try the homemade checkerberry ice cream while you’re at it.) By day, consider taking a beginner lesson from Liquid Dreams Surf Shop, and by night, try your hand at the classic arcade games at Fun-O-Rama.

When the sun is shining, Nantucket is where you’ll want to be soaking it up. Coastal charm and sea breezes await you here.

Eat at: Millie’s Restaurant in Madaket, offering West Coast twists on New England classics. Among them? Halibut ceviche, quesadillas filled with lobster, grilled zucchini and slow-roasted tomato, and fresh fish tacos. 

Stay at: The newly redesigned (and renamed) 76 Main Ink Press Hotel, which honors Nantucket’s history through its newspapers, magazines and authors in the former home of a salty sea captain. If you’re a devotee of the “Queen of Beach Reads,” consider booking the Elin Hilderbrand suite.

Must do: The island is best seen by bicycle. Rent one from Nantucket Bike Shop near the ferry terminal and explore to your heart’s content, from the beach to Cisco Brewers.

Make like a Gilded Age debutante and try a Newport summer on for size. While Newport is known for its famed mansions, there’s plenty else to see and do.

Eat at: Flora at the Gardiner House, to sample Mediterranean plates made with local seafood. The dining room is a pastel-colored treat for the eyes—with windows that open to let the breeze in from Newport Harbor.

Stay at: The Brenton Hotel in the heart of downtown Newport. A new sleep wellness program promises a restful weekend, offering guests a pillow menu, a sound bath meditation experience, and more.

Must do: If you haven’t stepped inside one, you must tour at least three of the Newport Mansions. (Save the Breakers for last—it’ll knock your socks off.) Afterward, stroll along the Cliff Walk to drink in views of the water.

The streets of Woodstock look like they’re pulled straight from the pages of a New England storybook. As one of the most charming towns in the region, Woodstock is best for an autumn escape. Aside from foliage, there are local farms, museums, and a traditional town square to behold.

Eat at: Worthy Kitchen, where you’ll find farm-to-table comfort food (smash burgers, potato salad, twice-fried chicken wings) and local craft beers on tap.

Stay at: Woodstock Inn & Resort, located right in Woodstock’s historic town square. Aside from its central location, it has a world-class spa and a small farm called Kelly Way Gardens where the inn grows most of its food.

Must do: Sugarbush Farm offers free cheese and maple syrup tastings. Head there to explore the farm grounds, see some animals, tour a sugarhouse, take in beautiful foliage views, and do a little shopping in their farm store.

Skip the sluggish Cape traffic and hop on a fast ferry over to Boston. In 90 minutes you’ll be strolling down Commercial Street, possibly with Portuguese fried dough in hand. 

Eat at: The Canteen, a laid-back spot with beachfront dining, an incredible cod banh mi, and frosé—in other words, a perfect P-Town meal.

Stay at: AWOL, a small, laid-back spot overlooking the bright-green marshes of the Province Lands. (Read: No noise from Commercial Street to interrupt your precious slumber.) There’s a pool here, not to mention a nightly fire in the fire pit.

Must do: It’s a classic for a reason. Stop by Art’s Dune Tours for an exhilarating ride through the dunes. The team gives you a full history of the area, with a rundown of the Cape Cod National Seashore and the story behind the area’s artist shacks. 

There’s one very important reason to go to Portland: to eat. This foodie city is teeming with excellent restaurants. The hard part will be deciding which ones to visit. 

Eat at: Once you’ve hit up Duckfat and Highroller Lobster Co., make a reservation for Mexican brunch at Ocotillo. Sip a one-of-a-kind cocktail at Sur Lie, or pose as a local and have lunch at the counter at Smalls. If you can make room in your schedule and your stomach, you’ll also want to order a steaming bowl of fresh pasta from Leeward.

Stay at: The Longfellow Hotel, a new independently owned boutique hotel right beside Tandem Coffee Roasters near the city’s West End. Its 48 rooms are ever so chic. There’s also The Press Hotel in Old Port, the former home of the Portland Press Herald. It recalls its print roots with newspaper-walls, letterpress carpeting, and typewriters galore. 

Must do: Hop on a boat in Casco Bay to explore Peaks Island, or drive up to Cape Elizabeth to see Portland Head Light.

If it’s fresh air you’re seeking, head west to the Berkshires, where you’ll find museums, concerts, historic homes, hiking, and much more. 

Eat at: Cello in Lenox for seasonally inspired dishes and friendly service, or see if there’s a pop-up to try from the community-minded After Hours.

Stay at: The Red Lion Inn, a wonderfully classic inn in Stockbridge. The subterranean bar, called the Lion’s Den, is fresh off a renovation and offers live music Thursday through Saturday.

Must do: Once you’ve explored MASS MoCA, head to The Clark in Williamstown for some more classical works. For a jaw-dropping house museum and garden tour, stop at Naumkeag, operated by the Trustees.

There is no place like the Kancamagus Highway, especially in the fall. This scenic road winds through the White Mountains and puts New England’s best foliage on display come the fall. There are a slew of charming small towns to stay in here, plus great hiking and skiing.

Eat at: Schilling Beer Co., a European-inspired craft brewery in the town of Littleton. Enjoy a wood-fired pizza and a German pilsner after a day spent on the trails.

Stay at: The Omni Mount Washington Resort, a hallmark of White Mountains luxury. This historic hotel has sweeping views of the Presidential Range. And across the street at Bretton Woods, you can take a gondola ride to the top of Mount Washington.

Must do: The Cog Railway, which allows you to take in the foliage from Mount Washington’s summit without having to do any of the work to get there. It takes you on a dramatic climb up the mountain, and has been doing so for more than 150 years.

Portland and Bar Harbor hog a lot of Maine’s attention, but the Midcoast region should not be slept on. Drive here for a classic Maine experience away from the crowds.

Eat at: As you make your way up north, take a detour for Alna Store, a market and restaurant with an ever-changing menu of local delicacies. Further ahead, set aside time to have an impressive yet unfussy meal Sammy’s Deluxe in Rockland, plus an afternoon for wine tasting at Oyster River Winegrowers.

Stay at: Tops’l Farm in Waldoboro, if you feel like glamping in a charming A-frame cabin. But if lightly roughing it is not your style, book a room at the newly renovated Norumbega in Camden. The library suite is really something special.

Must do: Visit Pemaquid Point Lighthouse Park with a can of Moxie in hand, or hike the stunning LaVerna Preserve in nearby Round Pond.

A short ferry ride from Wood’s Hole delivers you to the Vineyard. Whether Edgartown, Oak Bluffs, or Vineyard Haven is your home base, you’ll find lots to do and see in addition to the island’s picture-perfect beaches.

Eat at: Visit Back Door Donuts for the ultimate late-night snack. Trust us, these donuts are worth waiting in line for.

Stay at: The Harbor View Hotel cannot be beat. In addition to sumptuous accommodations, complimentary bikes and the Mercedes-Benz Drive Program make it an ultra-luxe home away from home. 

Must do: Behold the Aquinnah Cliffs Overlook. The red clay cliffs are a marvel on their own, but the sweeping views of the ocean (and Gay Head Light) aren’t bad, either.

Located just 13 miles off the coast of Rhode Island, Block Island is an excellent alternative to Nantucket or Martha’s Vineyard, as it’s quieter and a bit more relaxed. Nature lovers, gather ‘round: 40 percent of the island is covered with conservation land.

Eat at: Poor People’s Pub serves up local seafood, burgers, pizza, and more in a laid-back environment with a sizable patio. It’s also conveniently close to the Old Harbor Block Island Ferry terminal. 

Stay at: Spring House, the island’s oldest (and largest) hotel. Here, Adirondack chairs populate a wraparound veranda overlooking the water.

Must do: Go horseback riding on the beach. Visit Rustic Rides Horse Farm, which offers both beach rides and trail rides—clearly a unique way to see the island.

Join the throngs of witch-loving tourists and locals alike in Salem. The site of the Salem Witch Trials attracts thousands of visitors in the weeks leading up to Halloween, but it’s a solid trip to make any time of year, thanks to a sizable artist community, a buzzy drinking and dining scene, and plenty of coastal charm.

Eat at: Howling Wolf Taqueria, where you can sip a red-hot ghost pepper-infused margarita. This spot is known for massive burritos and their “wolf bites,” including avocado fries and ceviche. Wood-fired pizza at Bambolina is another solid option. 

Stay at: The Merchant, a chic boutique hotel in the heart of downtown. You’ll be walking distance to witchy shops galore, and when you’re tired of strolling, you can head to the hotel’s top floor, home to Salem’s only outdoor rooftop bar.

Must do: Fully embrace the spooky vibes by signing up for a Candlelit Ghostly Walking Tour. The hour-long journey guides you to some of Salem’s most haunted locations, including the Old Salem Prison. If you’ve gotten your fill of witch-adjacent attractions, visit the Peabody Essex Museum to see collections dating back to the 1700s.

A quick jaunt up from Boston, Kennebunkport is the ideal place for some weekend R&R. Soak up the sun, enjoy some seafood, and maybe even spot a member of the Bush family while you’re at it.

Eat at: Earth at Hidden Pond, a restaurant that zeroes in on “farm-to-fork” freshness with dishes like plumcot salad and mushroom lasagna. The setting is outstanding, too, with branches, fairy lights, and natural wood at every turn.

Stay at: Not much can compare to White Barn Inn, Auberge Resorts Collection, the epitome of coastal luxury for more than 150 years. In September 2024, the inn will launch the Cora Houseboat, a floating lodging on the Kennebunk River with ultra-stylish interiors.

Must do: Hop aboard a lobster boat with Rugosa Lobster Tours and try hauling up a lobster trap from the water yourself.

There comes a time in every Bostonian’s life when it makes sense to drive down to southern Connecticut. And when your time comes, spend that time eating pizza and admiring architecture in New Haven.

Eat at: A New Haven-style pie from Frank Pepe’s is not a choice but a must. Once you’ve had your fill of pizza, sample the Mediterranean tapas at Olea.

Stay at: The Brutalist beauty Hotel Marcel, designed by Bauhaus icon Marcel Breuer. The ultra eco-friendly hotel boasts repurposed light fixtures from the 1960s, among other midcentury charms. 

Must do: As the oldest college museum in the country, the Yale University Art Gallery displays an impressive collection of classics. It also happens to be free.

Stowe is a delight in every season, but it really comes alive in the wintertime when the skiers get to town. Even if you’re not a skier, there are maple creemees and après-ski cocktails to be enjoyed.

Eat at: Plate combines California cuisine with Vermont-sourced ingredients in the form of ramp and boursin soufflés and lobster Cobb salads. Also consider taking the gondola up to Cliff House atop Mount Mansfield—you can enjoy a bottle of wine on the deck before taking an equally scenic ride back down.

Stay at: Après-ski in style at Field Guide, a lodge in the heart of downtown. In spring, summer, and fall, consider Bluebird Cady Hill Lodge to serve as your home base for hiking and mountain biking.

Must do: Stop in the Alchemist brewery for a pint (or several) of Heady Topper.

Portland may get all the glory when it comes to New England’s weekend getaways, but Biddeford is a foodie destination in its own right. 

Eat at: Palace Diner to start. Devour a plate of buttermilk flapjacks at its 15-seat counter, then start making plans for lunch at Catface Cafe and dinner. In between, try a gin and tonic flight at Round Turn Distilling.

Stay at: The Lincoln Hotel, a 33-room boutique hotel housed inside a former mill. As a bonus hangout, there’s an outpost of Batson River Brewing and Distilling on the hotel’s lower level.

Must do: A little specialty grocery shopping before heading home. Stop in Nibblesford for Maine cheeses, Sweetcream Dairy for a pre-packed pint of brown butter crunch, and Edelweiss Pastry Shop for blueberry and orange brioche. 

In the summer, cruising out to Plum Island can certainly be squeezed into a day trip, but turning it into a breezy weekend is also a lovely idea. 

Eat at: Sunset Club, a casual open-air hangout serving beachy fare like jerk chicken wings, tuna poke bowls, and lobster rolls. Add in a tropical cocktail and you’ve got all the fixings for a perfect sunset viewing. 

Stay at: Blue Inn on the Beach, so you can skip the hassle of beach parking and while away your morning sipping coffee on a deck overlooking the ocean. 

Must do: Grab your binoculars and head for Parker River Wildlife Refuge for some rare shorebird watching. There are lots of gentle coastal walking trails to explore here. And on your way out, snap a pic of the iconic Pink House while you still can.

Five hours by car, Bar Harbor’s a bit further afield than the other destinations on this list. But it’s still an excellent choice for an outdoorsy weekend away from the city, thanks to New England’s only national park, Acadia. 

Eat at: Lompoc Cafe for a laid-back meal of lobster fritters and a dilly bean martini—all enjoyed from a leafy patio strung with lights.

Stay at: Terramor Outdoor Resort for a luxe glamping experience in the woods, or the Claremont for just the luxe part.

Must do: A tour of Acadia National Park, starting with a drive around the Park Loop Road. You can reserve a slot to drive to the top of Cadillac Mountain, too. And if it’s hiking you’re after, dare to try the Beehive Loop.

Another easy ride up I-95, Portsmouth packs loads of seaside charm (think: brick walkways, old Colonials, and bright-white church steeples) into its energetic downtown. 

Eat at: Botanica Restaurant and Gin Bar, for an upscale night out filled with French cuisine and plenty of gin.

Stay at: Hotel Thaxter, a stylish spot named for a young woman who romanticized island life while working at her family’s hotel on Appledore Island off the coast of Portsmouth.

Must do: Portsmouth has a smattering of excellent craft breweries within its relatively small footprint. Head over to Loaded Question Brewing Co. in the city’s West End; it’s housed within a former button factory.

You may need more than a weekend to discover all Providence has to offer, but you’ll certainly leave with a full belly (and heart!) after two days.

Eat at: Pizza Marvin, for a slice of “salad pizza” with a side of littlenecks. For your fill of seafood, head to raw bar Gift Horse for chilled lobster topped with nasturtiums and roe mayo.

Stay at: Graduate Providence, a recently renovated (and downright regal) hotel carved from the former Biltmore; the lobby is a true treat for the eyes. For a more boutique experience, try Dye House in Olneyville, which has “the broad barn door of a New England farm and the light-flooded interior of a Parisian loft,” according to its owners.

Must do: Visit the Roger Williams Park Zoo. It’s an oldie but a goodie, and the annual Jack-O-Lantern Spectacular is a twinkling treat come October.

When you’ve had your fill of fall in New England, head west for the Catskills for a new twist on small towns and mountain views. 

Eat at: Good Night, a South Asian spot in Woodstock with an impressive miso caesar salad, plus a dish with crispy egg noodles and local mushrooms.

Stay at: The Leeway, a new boutique luxury motel in Mount Tremper. The stylish riverfront getaway is ideal for fly-fishing and swimming, and offers complimentary yoga classes on the weekends.

Must do: Hike Overlook Mountain, then reserve a day for antique shopping and gallery-hopping around Woodstock and Phoenicia.

Outdoor adventures, excellent food, and stunning boutique lodgings await in northwestern Vermont.

Eat at: August First, for the best breakfast sandwich of your life and some delectable pastries. Make time to stop in Dedalus Wines, too, for a pet nat and some specialty cheeses.

Stay at: Blind Tiger Burlington, a stunningly chic boutique hotel housed in a brick mansion circa 1881. Pro tip: Sit on the patio overlooking the courtyard at breakfast time.

Must do: Rent bikes from Local Motion and bike the Island Line Trail, which extends into Lake Champlain via a narrow (and very scenic) causeway.

The Cape is a no-brainer, but where to stake your claim? Try the inimitable charms of Chatham, where the stately homes lined with hydrangea bushes will make your eyes widen, and the town center will present you with a boutique shop overload in the best possible way.

Eat at: The Impudent Oyster, which offers innovative spins on classic seafood dishes and a lively bar inside a former church. You have no choice but to stop in the Chatham Squire afterward for a nightcap.

Stay at: Chatham Bars Inn is the ne plus ultra of Cape retreats for good reason: The beach cabanas alone earn the resort its mythic reputation—and justifies the indulgence.

Must do: A seal cruise to Monomoy Island, where you can see these adorable creatures sunbathing on the beach. The boat ride also cruises past lighthouses and historic harbors, and your guide will give you a complete history of the area.