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

While Providence, Rhode Island, could easily fill more than a single weekend, two days in this vibrant city are certainly enough to leave you feeling completely satiated and charmed. It's a destination where culinary delights and rich cultural experiences abound.

Eat this: Pizza Marvin is a must-visit for a unique "salad pizza" paired perfectly with a side of fresh littlenecks. For a sophisticated seafood experience, head to Gift Horse Bar & Eatery, a vibrant raw bar where you can savor chilled lobster elegantly topped with nasturtiums and delicate roe mayo.

Stay here: Settle into Graduate by Hilton Providence, a regal hotel meticulously renovated from the historic Biltmore building; its grand lobby alone is a feast for the eyes. For a distinctively boutique experience, consider Dye House in the eclectic Olneyville neighborhood, a unique property whose owners describe it as possessing "the broad barn door of a New England farm and the light-flooded interior of a Parisian loft."

Do this: Spend an engaging day at the Roger Williams Park Zoo, a beloved and enduring attraction offering diverse exhibits and conservation efforts. As evening falls on (mostly) Saturdays from May through November, immerse yourself in the mesmerizing WaterFire Providence. The award-winning art installation illuminates the downtown rivers with over eighty sparkling bonfires, accompanied by world music and the fragrant scent of wood smoke. Also, carve out time to explore the RISD Museum (Rhode Island School of Design Museum), which boasts an incredibly diverse collection spanning ancient artifacts, Impressionist masterpieces, contemporary art, and unique design pieces from around the globe.

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 20mins from Boston

Another easy ride up I-95, Portsmouth, New Hampshire, packs loads of seaside charm into its energetic downtown. Picture this: quaint brick walkways, perfectly preserved old Colonial homes, and bright-white church steeples framing a bustling, walkable city center.

Eat this: For an upscale night out, immerse yourself in the sophisticated ambiance of Botanica Restaurant and Gin Bar, where refined French cuisine meets an extensive selection of gin. Moxy offers innovative New England-inspired tapas and cocktails in a stylish, lively setting with exposed brick and an open kitchen, celebrating Chef Matt Louis's creative approach to local ingredients.

Stay here: Settle into Hotel Thaxter, a stylish boutique hotel thoughtfully named for a young woman who found romance in island life while connected to her family's hotel on Appledore Island, just off the Portsmouth coast. This renovated historic building offers luxurious accommodations right in the heart of downtown.

Do this: Portsmouth boasts a smattering of excellent craft breweries within its relatively small footprint. Make your way to Loaded Question Brewing Co. in the city's West End, creatively housed within a former button factory, for a taste of their innovative brews. Beyond the breweries, immerse yourself in Portsmouth's vibrant independent shopping scene. Explore Nahcotta, a vibrant art gallery featuring unique original artwork and prints, perfect for finding a special piece. Gus & Ruby Letterpress boasts beautifully crafted stationery, cards, and curated gifts that truly capture Porthsmouth's charm. 

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.

1hr 30mins from Boston

For a quintessential coastal escape, Plum Island offers the ideal blend of laid-back charm, perfect for a relaxing day trip or an extended breezy weekend in Newbury. 

Eat this: Indulge in vibrant, open-air dining at Sunset Club, where beachy fare like savory jerk chicken wings, fresh tuna poke bowls, and classic lobster rolls are paired perfectly with tropical cocktails, setting the scene for an unforgettable sunset. Head to The Paddle Inn in nearby Newburyport, celebrated for its creative global small plates and lively, surf-inspired ambiance.

Stay here: Make Blue Inn on the Beach your coastal sanctuary, where direct beach access means you can bypass parking woes and begin your mornings with serene coffee sips from your deck, all while gazing at the endless ocean vista. For a more refined and historic stay, consider The Compass Rose Inn in downtown Newburyport, a beautifully restored Federal-style house offering elegant suites with features like fireplaces and a gourmet breakfast.

Do this: Equip yourself with binoculars and venture into the Parker River Wildlife Refuge, a prime spot for observing diverse and rare shorebird species amidst expansive, gentle coastal walking trails. For more wildlife fun, embark on a whale watching tour from the Newburyport waterfront with Newburyport Whale Watch.

1hr 40mins from Boston

While its more famous neighbor Portland often steals the spotlight, Biddeford, Maine, is quietly carving out its own reputation as a must-visit destination, particularly for the foodies among you.

Eat this: Kick off your culinary exploration at Palace Diner, an iconic 15-seat counter where you can savor their legendary buttermilk flapjacks. From there, grab lunch at Catface Cafe before exploring Biddeford's multitude of dinner options, such as Magnus on Water for Peruvian-inspired comfort food and inspiring cocktails, Fish & Whistle for delicious locally caught seafood or barbecue lovers paradise Ore Nell's Barbecue, where you'll find lipsmacking Texas-inspired barbecue. Mid-day, elevate your spirits with a unique gin and tonic flight at Round Turn Distilling.

Stay here: Settle into The Lincoln Hotel, a charming 33-room boutique property thoughtfully transformed from a historic mill. You'll find an inviting outpost of Batson River Brewing and Distilling located conveniently on the hotel’s lower level, perfect for an evening unwind.

Do this: Explore Biddeford's revitalized historic mill district and stroll along the RiverWalk, offering picturesque views and a chance to discover the creative businesses housed within these repurposed industrial spaces. Before departing, dedicate time to some exceptional specialty grocery shopping. Stock up on exquisite Maine cheeses at Nibblesford, grab a pre-packed pint of their signature brown butter crunch ice cream from Sweetcream Dairy, and treat yourself to delectable blueberry and orange brioche from Edelweiss Pastry Shop.

1hr 45mins from Boston

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

Eat this: Indulge at The Impudent Oyster, which offers innovative spins on classic seafood dishes within a lively bar setting inside a former church. You have no choice but to stop in the Chatham Squire afterward for a quintessential Cape Cod nightcap. Del Mar Bar & Bistro offers upscale American cuisine with fresh seafood and wood-fired pizzas.

Stay here: Chatham Bars Inn remains the ne plus ultra of Cape retreats for good reason: Its luxurious beach cabanas alone earn the resort its mythic reputation and justify the indulgence. For another sophisticated option, consider the Greyfinch Chatham Inn, a beautifully renovated boutique hotel offering a modern coastal retreat just minutes from the town's best beaches and shops.

Do this: Embark on a memorable seal cruise with Monomoy Island Excursions to witness adorable seals sunbathing on the beach. The boat ride also cruises past historic lighthouses and charming harbors, with your guide providing a complete history of the area. For another authentic Chatham experience, head down to the Chatham Pier Fish Market. Here, you can watch local fishermen bring in their daily catch, often attracting curious seals hoping for a snack, and even grab some fresh seafood or a lobster roll right off the boat.

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. 

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 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. 

2hrs 30mins from Boston

New Haven, Connecticut, the home of Yale University, is renowned for its iconic pizza and impressive architecture, making it a worthwhile getaway for foodies and culture hounds, alike. 

Eat this: A visit to New Haven wouldn't be complete without experiencing an authentic New Haven-style pizza. Your first stop should be Frank Pepe’s, where a classic "apizza" is an absolute must-try. After indulging in the local specialty, broaden your palate with the exquisite Mediterranean tapas at Olea.

Stay here: Immerse yourself in architectural history by staying at the Hotel Marcel, a stunning example of Brutalist design by Bauhaus icon Marcel Breuer that has been transformed into an ultra eco-friendly hotel. You'll appreciate its midcentury charm, including repurposed light fixtures from the 1960s, seamlessly blended with modern and innovative sustainable elements. The Blake Hotel, a chic boutique property known for its stylish interiors and a popular rooftop bar, offers a luxurious experience downtown.

Do this: If you're in New Haven, you've gotta visit Yale University, a wonderland for enthusiasts of art, design and architecture. The Yale University Art Gallery is the nation's oldest college museum. It houses an extensive and impressive collection of masterpieces spanning various eras and styles, and admission is completely free. After that, wander into the Beinecke Rare Book and Manuscript Library, an architectural marvel housing a remarkable collection of ancient texts such as a Gutenberg Bible and a facsimile of the mysterious Voynich Manuscript, all viewable in its unique exhibition hall. For an enlightening experience outside Yale, head to Lighthouse Point Park, where you can enjoy scenic views of Long Island Sound, ride the historic carousel, and explore the iconic lighthouse.

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.

3hrs 15mins from Boston

Stowe, Vermont, offers appeal in every season, yet truly shines when winter blankets the landscape and skiers descend upon the town. Even if hitting the slopes isn't your priority, there's plenty to savor, from local maple creemees to lively après-ski gatherings.

Eat this: Head to Plate, where California-inspired cuisine meets Vermont's freshest ingredients. Expect inventive dishes like ramp and boursin soufflés or refreshing lobster Cobb salads. Doc Ponds is a hopping gastropub with elevated gastropub fare using local ingredients, featuring smash burgers, inventive small plates, and a fantastic craft beer selection. Don't leave town without trying a classic Vermont maple creemee at local go-to Red Barn Ice Cream Shop.

Stay here: Indulge in stylish après-ski relaxation at Field Guide, a charming lodge nestled right in the heart of downtown Stowe. For those visiting in the warmer months—spring, summer, or fall—Bluebird Cady Hill Lodge makes an ideal home base, perfectly situated for accessing the area's best hiking and mountain biking trails.

Do this: A visit to Stowe wouldn't be complete without a stop at The Alchemist brewery. Sample their renowned Heady Topper, a local favorite, and discover why this craft brewery has gained a cult following. For gorgeous views, take a scenic gondola ride up Mount Mansfield to Cliff House, where you can enjoy a fine bottle of wine on the deck before an equally picturesque journey back down the mountain.

3hrs 45mins from Boston

When the familiar charm of New England's fall begins to wane, turn your gaze westward to the Catskills, where a distinct blend of quaint mountain towns and stunning vistas offers a refreshing new perspective on autumnal escapes.

Eat this: Indulge your palate at Good Night in Woodstock, a celebrated South Asian eatery where you'll discover inventive dishes like their remarkably flavorful miso caesar salad, alongside unique creations such as crispy egg noodles perfectly complemented by foraged local mushrooms. Silvia, a New American restaurant also in Woodstock, is renowned for its focus on locally sourced, seasonal ingredients prepared on a wood-fired grill in a vibrant open-kitchen setting.

Stay here: Discover tranquility and style at The Leeway, a new boutique luxury motel nestled along the riverfront in Mount Tremper. This elegant getaway provides an ideal setting for serene activities like fly-fishing and swimming, further enhanced by complimentary weekend yoga classes for guests. For a distinctive, Scandi-inspired retreat amidst the mountains, consider Eastwind Oliverea Valley, known for its stylish Lushna glamping cabins and hotel rooms, complete with amenities like saunas and an on-site restaurant.

Do this: Challenge yourself with a rewarding hike up Overlook Mountain, boasting incredible panoramic views. Afterward, dedicate a full day to exploring the eclectic charm of Woodstock and Phoenicia, where you can browse unique antique shops for hidden treasures and immerse yourself in vibrant local art by gallery-hopping.

3hrs 45mins from Boston

Outdoor adventures, excellent food, and stunning boutique lodgings await in northwestern Vermont. Nestled on the vibrant shores of Lake Champlain, Burlington offers a dynamic blend of urban charm and immediate access to breathtaking natural beauty. It’s an ideal destination for those seeking a lively city escape seamlessly combined with abundant opportunities for outdoor exploration.

Eat this: Start your day right at August First, renowned for crafting what might just be the best breakfast sandwich you'll ever encounter, perfectly paired with their delectable, freshly baked pastries. Head to Honey Road, celebrated for its Eastern Mediterranean mezze in a chic and lively setting. If you're seeking a unique bottle, check out The Archives, a combination arcade and bar known for its curated selection of craft brews and inventive cocktails. 

Stay here: Indulge in refined comfort at Blind Tiger Burlington, a stunningly chic boutique hotel gracefully housed within a meticulously restored brick mansion dating back to 1881. For an extra touch of charm, be sure to claim a spot on the serene patio overlooking the courtyard during breakfast.

Do this: Embrace Burlington’s outdoor spirit by renting bikes from Local Motion and embarking on a ride along the captivating Island Line Trail. This unique path extends dramatically into Lake Champlain via a narrow, incredibly scenic causeway, offering unforgettable waterfront views and a truly immersive experience. Looking for activities on your own two feet? Dive into Burlington's diverse independent shopping scene. Discover locally made treasures at Frog Hollow Vermont Craft Gallery, showcasing exquisite Vermont artistry. Browse a fantastic selection of new and used books at Crow Bookshop, a beloved independent bookstore. And for all your outdoor adventure needs, from hiking to biking gear, explore the extensive selection at Outdoor Gear Exchange, a local favorite for adventure enthusiasts.

5hrs from Boston

Though a longer journey at five hours by car, Bar Harbor, Maine, promises an unparalleled escape into nature. This charming coastal town serves as the perfect base for an unforgettable outdoorsy weekend, primarily thanks to its direct access to Acadia National Park, New England's sole national park.

Eat this: For a quintessential laid-back Bar Harbor experience, dine at Lompoc Cafe. Their inviting, leafy patio, adorned with charming string lights, provides the perfect ambiance to savor unique offerings like crispy lobster fritters alongside a distinctive dilly bean martini. Thirsty Whale Tavern is a beloved local spot known for its classic Maine seafood dishes, including some of the best lobster rolls and steamed mussels around, all in a lively, casual atmosphere.

Stay here: Opt for an elevated wilderness retreat at Terramor Outdoor Resort, where luxurious glamping tents, with high-quality Frette linens and cozy Pendleton blankets, ensuite bathrooms (in most tents) and your own screened-in porch and fire pit, provide a refined experience nestled in the woods. For a full-on hotel experience, The Claremont offers sophisticated and luxe stays within a quick drive from Bar Harbor. 

Do this: Immerse yourself in the breathtaking landscapes of Acadia National Park. Begin your exploration with a scenic drive along the iconic Park Loop Road, and be sure to reserve a vehicle slot if you plan to ascend to the panoramic summit of Cadillac Mountain. For hikers seeking a challenge, dare to tackle the Beehive Loop Trail, renowned for its tough climbs and stunning vistas.