23 best weekend getaways from Boston

40mins from Boston

Join the spirited mix of witch-loving tourists and curious locals in Salem. While the historic site of the Salem Witch Trials draws thousands during the lead-up to Halloween, it offers a compelling visit any time of year—thanks to a thriving artist community, a vibrant dining and drinking scene, and abundant coastal charm.

Eat here: Head to Howling Wolf Taqueria, where you can brave a red-hot ghost pepper-infused margarita. This popular spot is celebrated for its generously sized burritos and their addictive "wolf bites," which include crispy avocado fries and refreshing ceviche. For another excellent choice, savor wood-fired pizza at Bambolina. For a casual meal, head to Ledger Restaurant, housed in a beautifully restored historic bank building, offering contemporary American cuisine with a focus on wood-fired dishes. 

Stay here: Check into The Merchant, a chic boutique hotel perfectly situated in the heart of downtown. From here, you'll be just a stroll away from countless witchy shops. When your feet tire, ascend to the hotel's top floor, home to Salem's only outdoor rooftop bar.

Do this: Fully embrace the eerie atmosphere by signing up for a Candlelit Ghostly Walking Tour. This hourlong journey will guide you to some of Salem's most haunted locations, including the historic Old Salem Prison. If you've had your fill of witch-adjacent attractions, explore the Peabody Essex Museum to discover impressive collections dating back to the 1700s.

1hr from Boston

Portland, Maine, beckons with a singular, compelling invitation—to eat! This vibrant city is a mecca for food enthusiasts, overflowing with exceptional of restaurants. Your only challenge will be selecting which one to eat at.

Eat here: After indulging in the delights of Duckfat and Highroller Lobster Co., secure a reservation for a memorable Mexican brunch at Ocotillo. For a unique libation, sip a handcrafted cocktail at Sur Lie. To experience Portland like a local, grab a counter seat for lunch at Smalls. If your schedule and appetite permit, don't miss the opportunity to savor a steaming bowl of fresh pasta from Leeward.

Stay here: Consider a stay at The Longfellow Hotel, a chic, newly opened, independently owned boutique hotel perfectly situated beside Tandem Coffee Roasters near the city's West End. Its 48 rooms exude sophisticated charm. Alternatively, experience The Press Hotel in Old Port. This distinctive establishment, once home to the Portland Press Herald, proudly showcases its print heritage with newspaper-adorned walls, letterpress-inspired carpeting, and an abundance of vintage typewriters.

Do this: Embark on a scenic boat trip across Casco Bay to explore the charming Peaks Island. Or, take a short drive to Cape Elizabeth to witness the iconic Portland Head Light—a quintessential New England lighthouse.

1hr 15mins from Boston

York, Maine, is just a little over an hour's drive from Boston, yet it feels like stepping into a whole different world. This charming beach town perfectly captures the essence of a New England summer—think sunshine, sandy shores, and delectable saltwater taffy—without the hassle of a long journey.

Eat here: For a lively meal with stunning views, head to Stones Throw, overlooking Long Sands Beach. Their spicy Thai coconut mussels and savory falafel are must-tries. You can even grab a canned cocktail to go! For another excellent option in York, consider The Central Restaurant & Bar. Don't let its strip-mall location fool you; this year-round spot offers an eclectic, internationally influenced menu with delicious hardwood-grilled entrées and small plates. 

Stay here: The recently opened Viewpoint Hotel boasts breathtaking shoreside rooms that offer an unparalleled New England vista: a picture-perfect view of Nubble Lighthouse. These rooms are ingeniously built into the Cape Neddick hillside, maximizing the iconic landmark with floor-to-ceiling windows. If a classic beach getaway is more your speed, consider settling into The Nevada motel, the Viewpoint's newly restored sister property, which reopened in July 2024.

Do this: A visit to York wouldn't be complete without a stop at The Goldenrod. Watch as saltwater taffy is stretched in the window, then pull up a stool at their old-fashioned soda counter. Be sure to try the homemade checkerberry ice cream! During the day, unleash your inner surfer with a beginner lesson from Liquid Dreams Surf Shop. As evening falls, challenge your friends to classic arcade games at Fun-O-Rama.

1hr 20mins from Boston

Envision yourself as a character from the The Gilded Age, stepping into a Newport summer. While this iconic Rhode Island city is celebrated for its legendary mansions, there's a wealth of other experiences to enjoy

Eat here: At Flora in the Gardiner House, prepare for a delightful culinary journey featuring Mediterranean-inspired dishes crafted with the freshest local seafood. The dining room itself is a pastel-hued dream, with expansive windows that invite in the refreshing seabreezes from Newport Harbor. 

Stay here: Discover the Brenton Hotel, ideally situated in the vibrant heart of downtown Newport. This hotel elevates the concept of a restful getaway with its innovative sleep wellness program, offering guests a unique pillow menu, a serene sound bath meditation experience, and other thoughtful amenities designed for ultimate chill. 

Do this: A trip to Newport wouldn't be complete without immersing yourself in the opulence of the past. Be sure to tour at least three of the magnificent Newport Mansions. We highly recommend saving The Breakers for last—its grandeur is truly breathtaking. Afterward, embrace the refreshing ocean air with a leisurely stroll along the scenic Cliff Walk, where dramatic coastal views meet architectural masterpieces. Note that there may be some detours on the Cliff Walk due to ongoing repairs, but the majority remains open.

1hr 30mins from Boston

Kennebunkport is your perfect weekend retreat from Boston for some rest and relaxation. Here, you can bask in the sunshine, savor delicious seafood, and maybe even catch a glimpse of the Bush family.

Eat here: Earth at Hidden Pond offers an exceptional "farm-to-fork" experience with dishes like plumcot salad and mushroom lasagna. The ambiance is magical, with branches, fairy lights, and natural wood at every turn. Located in a chic hotel overlooking the Kennebunk River, The Boathouse Restaurant is known for putting exciting twists on New England flavors, with a focus on fresh Maine seafood infused with Asian influences. It's also a go-to spot for creative craft cocktails.

Stay here: For unparalleled coastal luxury, the White Barn Inn & Spa has been a top choice for over 150 years. In September 2024, they're introducing the Cora Houseboat, a chic floating accommodation right on the Kennebunk River. The Kennebunkport Inn, a classic, cozy hilltop retreat located centrally in Dock Square, is historic mansion turned inn that offers a warm welcome and is just steps away from boutique shopping, riverside strolls and charming coffeehouses.

Do this: Embark on an authentic maritime adventure with Rugosa Lobster Tours. You can hop aboard a lobster boat and even try your hand at hauling up a lobster trap from the water. Another fun option is to take a scenic drive along Ocean Avenue. This picturesque route offers breathtaking ocean vistas, views of the iconic Walker's Point (the Bush family compound), and dramatic natural formations like Spouting Rock and Blowing Cave.

2hrs from Boston

Escape to Woodstock, Vermont, where the streets appear as if plucked directly from a classic New England tale. Renowned as one of the region's most captivating towns, Woodstock (not to be confused with Woodstock, New York, where the famed music festival was held) shines brightest as an autumn retreat. Beyond the breathtaking foliage, discover local farms, intriguing museums, and a picturesque town square.

Eat here: Savor the taste of authentic farm-to-table comfort food at Worthy Kitchen. Its menu boasts juicy smash burgers, creamy potato salad, and perfectly twice-fried chicken wings, all complemented by an excellent selection of local craft beers on tap. 

Stay here: Immerse yourself in luxury and convenience at the Woodstock Inn & Resort, perfectly situated in Woodstock's historic town square. Beyond its prime location, the Inn features a world-class spa for ultimate relaxation and Kelly Way Gardens, a small farm on-site where much of the Inn's fresh produce is grown. 

Do this: A visit to Sugarbush Farm is a must for any visitor. Enjoy complimentary tastings of their delicious cheese and maple syrup. Explore the sprawling farm grounds, meet some friendly animals, take a tour of their sugarhouse, soak in the stunning foliage views, and pick up some local treats at their farm store. 

2hrs 20mins from Boston

Leave the sluggish Cape traffic behind and opt for a swift ferry ride over to Provincetown. In just 90 minutes, you could find yourself leisurely strolling down Commercial Street, perhaps with a warm Portuguese fried dough in hand. Remember, P-Town is very much a seasonal destination, with everything typically up and running from late-May through Halloween. Outside of that, it's kind of a no-man's land. 

Eat here: Grab a bite at The Canteen, a wonderfully laid-back establishment offering direct beachfront dining. Their menu features an incredible cod banh mi and refreshing frosé—truly the makings of a perfect P-Town meal. 

Stay here: Settle into AWOL, a tranquil, relaxed retreat boasting views of the verdant marshes of the Province Lands. This means peaceful slumber, undisturbed by the buzz of Commercial Street. AWOL also offers a inviting pool and a delightful nightly fire pit. 

Do this: It's a classic for a reason: Embark on an exhilarating journey with Art's Dune Tours through the iconic dunes. The knowledgeable team provides a fascinating history of the area, including insights into the Cape Cod National Seashore and the intriguing tales behind the local artist shacks. 

1hr 30mins + 1hr fast ferry ride from Boston

When the Nantucket sun graces the island, that's precisely where you'll want to bask in its glow. Prepare to be enchanted by its quintessential coastal charm and invigorating sea breezes.

Eat here: Indulge your palate at Millie's Restaurant in Madaket, a beloved institution offering a delightful West Coast interpretation of New England culinary traditions. Their menu features innovative dishes like halibut ceviche, lobster, grilled zucchini, and slow-roasted tomato quesadillas, and of course, their renowned fresh fish tacos. 

Stay here: Immerse yourself in Nantucket's rich heritage at the recently redesigned and renamed 76 Main Ink Press Hotel. This elegant establishment, once the residence of a venerable sea captain, now pays homage to the island's journalistic and literary past through its decor, inspired by newspapers, magazines, and Nantucket's celebrated authors. If you're a fan of the "Queen of Beach Reads," you might even consider booking the exclusive Elin Hilderbrand suite. 

Do this: The ultimate way to experience the island's beauty is by bicycle. Rent some wheels from Young's Bicycle Shop, conveniently located near the ferry terminal, and embark on an exploration that will take you from the pristine beaches to the lively atmosphere of Cisco Brewers. 

1hr 30mins + 45min ferry from Boston

A brief ferry journey from Woods Hole transports you directly to Martha's Vineyard. Whether you choose Edgartown, Oak Bluffs, or Vineyard Haven as your primary base, you'll discover a wealth of activities and sights to enjoy, perfectly complementing the island's postcard-perfect beaches.

Eat here: For an exceptional dining experience with a focus on fresh, local ingredients, visit State Road Restaurant in West Tisbury, known for its refined American cuisine in a charming, rustic setting. In Edgartown, don't miss Larsen's Fish Market for some of the freshest seafood around—a true island institution for lobster, steamers, and fresh-off-the-boat catches. Make your way to Back Door Donuts for the quintessential late-night indulgence. Trust us—these donuts are absolutely worth the queue.

Stay here: The Harbor View Hotel is simply unparalleled. Beyond its lavish accommodations, thoughtful touches like complimentary bikes and the Mercedes-Benz Drive Program transform it into an ultra-luxurious home away from home.

Do this: Marvel at the Aquinnah Cliffs Overlook. The distinctive red clay cliffs are a spectacle in themselves, while the expansive ocean views—including the majestic Gay Head Light—are equally captivating.

2hrs 30mins from Boston

For those craving fresh air and cultural enrichment, a journey west to the Berkshires offers an abundance of museums, captivating concerts, historic estates, scenic hiking trails …

Eat here: Indulge in seasonally inspired dishes and warm hospitality at Cello in Lenox. Alternatively, keep an eye out for unique culinary experiences from the community-focused After Hours, which frequently hosts pop-up events.

Stay here: Settle into the timeless charm of The Red Lion Inn, a quintessential New England inn nestled in Stockbridge. Be sure to visit their subterranean bar, the Lion's Den, which has recently undergone a renovation and features live and DJ-spun music from Wednesday through Sunday.

Do this: After exploring the contemporary art wonders at MASS MoCA, immerse yourself in more classical works at The Clark in Williamstown. For a truly breathtaking house museum and garden tour, make a stop at Naumkeag, meticulously operated by the Trustees.

2hrs 30mins from Boston

There's truly no destination quite like the Kancamagus Highway, particularly when autumn paints the landscape. This breathtaking scenic route meanders through the majestic White Mountains, showcasing New England's most spectacular fall foliage. Along its path, you'll discover a collection of charming small towns perfect for lodging, alongside fantastic opportunities for hiking and skiing.

Eat here: Discover Schilling Beer Co., a European-inspired craft brewery nestled in the town of Littleton. After a day spent traversing the trails, unwind with a delicious wood-fired pizza and a crisp German pilsner.

Stay here: Experience the epitome of White Mountains luxury at Omni Mount Washington Resort, a historic hotel offering sweeping vistas of the Presidential Range. Just across the street at Bretton Woods, you can ascend to the summit of Mount Washington via a scenic gondola ride.

Do this: Embark on a memorable journey aboard The Cog Railway, allowing you to soak in the panoramic foliage views from Mount Washington's peak without the effort of the climb. This iconic railway has been providing a dramatic ascent up the mountain for over 150 years.

2hrs + 1hr ferry ride from Boston

Block Island, a serene escape just 13 miles from Rhode Island's coast, offers a tranquil alternative to the bustling scenes of Nantucket or Martha’s Vineyard. It's a paradise for nature enthusiasts, with a remarkable 40% of the island dedicated to conservation land.

Eat here: For a relaxed meal featuring local seafood, burgers, and pizza, head to Poor People’s Pub. It boasts a spacious patio and is conveniently near the Old Harbor Block Island Ferry terminal. Grab a seat at Winfield's when you crave fine dining with an international flair; its menu is influenced by French, Italian, New American, and Asian cuisines, all served in a cozy, elegant setting.

Stay here: Consider the Spring House, the island’s oldest and largest hotel. Its charming wraparound veranda, adorned with Adirondack chairs, provides picturesque water views. Alternatively, the Block Island Beach House offers a boutique hotel experience with beachfront rooms, some with private balconies, and is just steps from lively downtown.

Do this: Experience the island from a unique perspective by horseback riding on the beach. Rustic Rides Horse Farm offers both scenic beach and trail rides. For another adventurous option on your own two feet, head to Mohegan Bluffs, where you can marvel at dramatic 200-foot cliffs and descend 141 steps to a secluded beach below.

3hrs from Boston

While Portland and Bar Harbor often capture the lion's share of Maine's spotlight, the Midcoast region is a truly unmissable gem. Head north to this picturesque stretch for an authentic Maine experience, far from the bustling crowds.

Eat here: As your journey progresses northward, consider a delightful detour to Alna Store—a charming market and restaurant boasting an ever-evolving menu of exquisite local delicacies. Further along, carve out time for an impressive yet unpretentious meal at Sammy's Deluxe in Rockland. Don't forget to dedicate an afternoon to wine tasting at Oyster River Winegrowers.

Stay here: For a unique glamping experience, book one of the charming A-frame cabins at Tops'l Farm in Waldoboro. If a touch of ruggedness isn't quite your style, secure a room at the newly renovated Norumbega in Camden—their library suite, in particular, offers something truly special.

Do this: Visit the iconic Pemaquid Point Lighthouse Park with a can of Moxie in hand, or embark on a invigorating hike through the stunning LaVerna Preserve in nearby Round Pond.

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.