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 shopping and dining scene, and abundant coastal charm when you step away from the town center.

Eat here: For classic New England seafood with deep local roots, book a table at Turner’s Seafood, a longtime Salem favorite housed in historic Lyceum Hall. The menu leans traditional in the best way, with impeccably fresh oysters, clam chowder, lobster rolls and expertly prepared whole fish, all served in a lively, welcoming setting that feels quintessentially coastal. You could also go the wood-fired pizza route at Bambolina, or opt for a more casual meal at Ledger Restaurant, set inside a beautifully restored historic bank building and known for its contemporary American fare.

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 excellent Peabody Essex Museum to discover impressive collections dating back to the 1700s.

1hr 15mins from Boston

While Providence, Rhode Island, could easily fill more than a single weekend, two days is plenty of time to soak up this arty city’s charm. It packs an outsized punch when it comes to food, arts and culture, making it an ideal quick getaway.

Eat this: Scope out some of Providence’s James Beard–recognized restaurants, starting with Pizza Marvin, known for its cult-favorite “salad pizza” paired with fresh littlenecks. For a more refined seafood experience, head to Gift Horse Bar & Eatery, a lively raw bar serving pristine oysters and chilled lobster finished with thoughtful, seasonal touches. For cocktails, make a stop at Loma, a moody, design-forward bar that’s quickly become a local favorite. 

Stay here: For a central base, book a room at The Beatrice, a polished boutique hotel in the heart of downtown, ideal for walking to restaurants, shops and cultural attractions. For more of a neighborhood setting, check into Dye House in Olneyville, one of Providence’s most creative, post-industrial neighborhoods, where a quieter, more local feel replaces the bustle of the city center.

Do this: Spend a day at Roger Williams Park Zoo, a longtime local favorite with expansive exhibits and a strong focus on conservation. On select Saturdays from May through November, experience WaterFire Providence, when more than 80 bonfires illuminate the city’s rivers to the sound of world music and the scent of wood smoke—it's a New England must. Also make time for the RISD Museum (Rhode Island School of Design Museum), home to a wide-ranging collection that spans ancient artifacts, Impressionist works, contemporary art and global design. 

1hr 15mins from Boston

York is just over an hour’s drive from Boston, yet it feels like stepping into a different world. This charming beach town captures the essence of a New England summer—think sunshine, sandy shores and 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, and you can even grab a canned cocktail to go. If you’re craving something beyond beach-town fare, make your way to The Central Restaurant & Bar (which typically takes a winter break in January and February). Don’t let its strip-mall location fool you; this longtime local favorite serves an eclectic, internationally influenced menu of hardwood-grilled entrées and small plates. 

Stay here: The recently overhauled Viewpoint Hotel offers breathtaking shoreside rooms with glass walls that frame a picture-perfect view of Nubble Lighthouse at nearly every angle. If a more classic beach stay is your style, book a room at The Nevada, the Viewpoint’s newly restored sister motel, with a laid-back, retro beach feel.

Do this: A visit to York wouldn’t be complete without a stop at The Goldenrod—a beloved summer staple where you can watch saltwater taffy being stretched in the window before pulling up a stool at the old-fashioned soda counter. (The homemade checkerberry ice cream is a must.) During the warmer months, catch a wave with a beginner lesson from Liquid Dreams Surf Shop, then wind down with classic arcade games at Fun-O-Rama. Note: Many of York’s attractions operate seasonally and typically close during the winter months.

1hr 20mins from Boston

Envision yourself as a character from The Gilded Age, stepping into a Newport summer. While this iconic Rhode Island city is best known for its legendary mansions, there’s far more to experience—from coastal walks and sailing culture to a lively shopping, dining and bar scene that keeps the town buzzing well beyond mansion tours.

Eat here: For a splurge night, pre-book a table at one of Newport’s two 2026 James Beard–nominated restaurants: Giusto for a refined Italian meal centered on handmade pastas, or Audette for a more chef-driven experience focused on thoughtful, seasonal tasting menus. For something breezier, Flora delivers Mediterranean-inspired dishes built around fresh local seafood in a pastel-hued dining room overlooking the harbor. Local favorite White Horse Tavern offers a more relaxed, classic Newport experience in a warm, unfussy setting.

Stay here: For a modern, waterfront stay within easy walking distance of downtown, book a room at Brenton Hotel, a sleek boutique property with harbor views and a relaxed, contemporary feel. If you’re after old-school Newport grandeur, The Chanler at Cliff Walk delivers dramatic oceanfront scenery and old-world romance. 

Do this: No trip to Newport is complete without stepping into its Gilded Age past—plan to tour at least a few of the Newport Mansions, saving The Breakers for last, when the scale and spectacle really land. Follow that up with a stroll along the Cliff Walk, where dramatic ocean views meet some of the city’s most impressive architecture (note that limited detours may be in place due to ongoing repairs). Back in town, spend time wandering Thames Street, Newport’s lively main drag, lined with shops, galleries, cafés and bars that make it easy to linger.

1hr 20mins from Boston

An easy ride up I-95, Portsmouth, New Hampshire, packs plenty of seaside charm into its energetic downtown. Expect quaint brick walkways, beautifully preserved Colonial homes and bright-white church steeples framing a lively, highly walkable city center.

Eat here: For an upscale night out, settle into Botanica Restaurant and Gin Bar, where refined French cooking meets an impressively deep gin list. For something livelier, Moxy serves inventive New England–inspired tapas and cocktails in a buzzy space with exposed brick and an open kitchen, showcasing chef-driven takes on local ingredients.

Stay here: Rest your head at Hotel Thaxter, a stylish boutique hotel named for Celia Thaxter, the 19th-century poet who spent her childhood and many summers on Appledore Island (which makes for a lovely day trip in warmer months), just off the Portsmouth coast. Housed in a thoughtfully renovated historic building, the hotel offers polished, comfortable rooms right in the heart of downtown.

Do this: Portsmouth punches above its weight when it comes to craft beer, with several excellent breweries packed into a compact downtown. Sample some of its best small-batch brews at Loaded Question Brewing Co. in the West End, creatively housed in a former button factory. Beyond the beer scene, dive into Portsmouth’s strong independent shopping culture. Browse Nahcotta, a bright gallery showcasing original artwork and prints, then stop by Gus & Ruby Letterpress for beautifully made stationery, cards and thoughtfully curated gifts that capture the city’s creative spirit. 

1hr 30mins from Boston

Kennebunkport makes for an easy, crowd-pleasing weekend escape from Boston—especially if rest and relaxation are on the agenda. Think sandy beaches, classic Maine seafood and slow afternoons by the water, with just enough polish to keep things feeling special. And yes, you might even spot a member of the Bush family while you’re there.

Eat here: For a special night out, book a table at Earth at Hidden Pond, where a true farm-to-fork philosophy shines through dishes like plumcot salad and mushroom lasagna. The dining room feels almost enchanted, with branches, soft lighting and natural wood woven throughout. For something closer to the water, head to The Boathouse Restaurant, a stylish spot overlooking the Kennebunk River that puts creative twists on New England flavors, spotlighting fresh Maine seafood with subtle Asian influences—along with standout craft cocktails.

Stay here: For classic coastal luxury, White Barn Inn & Spa remains the gold standard, pairing old-world elegance with serene riverfront surroundings. One of its standout offerings is the Cora Houseboat, a chic floating accommodation docked on the Kennebunk River that adds a distinctly modern twist to the historic property. For a more central stay, Kennebunkport Inn is a cozy, historic mansion-turned-inn perched just above Dock Square, putting boutique shopping, riverside walks and local coffeehouses at your doorstep.

Do this: Get out on the water with Rugosa Lobster Tours for a hands-on introduction to Maine’s lobster industry—you’ll cruise aboard a working lobster boat and even have the chance to help haul a trap from the sea. Back on land, take a scenic drive along Ocean Avenue, where sweeping ocean views give way to landmarks like Walker's Point and dramatic natural features including Spouting Rock and Blowing Cave.

1hr 30mins from Boston

For a quintessential coastal escape, Plum Island delivers laid-back beach-town charm that works just as well for a relaxed day trip as it does for a breezy weekend away. Part of Newbury, the barrier island is all about sandy dunes, salty air and slowing down by the shore.

Eat this: Lean into the beachy vibe at Sunset Club, a seasonal, open-air favorite where jerk chicken wings, tuna poke bowls and classic lobster rolls are paired with tropical cocktails—best enjoyed as the sun dips over the dunes. For a change of pace, head inland to The Paddle Inn in nearby Newburyport, known for its creative, globally inspired small plates and lively, surf-leaning atmosphere.

Stay here: Make Blue Inn on the Beach your coastal base, where direct beach access lets you skip parking altogether and start the day with coffee on your deck, looking out over the open ocean. For a more refined, historic stay nearby, book a room at The Compass Rose Inn, a beautifully restored Federal-style home in downtown Newburyport offering elegant suites—some with fireplaces—and a standout gourmet breakfast.

Do this: Bring binoculars and head into Parker River Wildlife Refuge, a standout destination for spotting shorebirds and other wildlife along wide, flat coastal trails that are easy to explore at your own pace. For a bigger adventure, set out on a whale-watching tour from the Newburyport waterfront with Newburyport Whale Watch, where seasonal cruises offer the chance to see whales feeding just offshore.

1hr 40mins from Boston

While its better-known neighbor Portland often steals the spotlight, Biddeford is quietly building a name for itself—especially among food lovers. The former mill town has emerged as one of southern Maine’s most exciting dining destinations, with creative kitchens and a distinctly local, under-the-radar feel.

Eat this: Start your culinary crawl at Palace Diner, the iconic 15-seat counter known for its legendary buttermilk flapjacks. From there, grab lunch at Catface Café before diving into Biddeford’s excellent dinner scene. Top picks include Magnus on Water for Peruvian-inspired comfort food and inventive cocktails, Fish & Whistle for locally caught seafood, and Ore Nell’s Barbecue for lip-smacking Texas-style barbecue. In between meals, stop by Round Turn Distilling for a gin-and-tonic flight that showcases the distillery’s creative spirits.

Stay here: Settle into The Lincoln Hotel, a 33-room boutique property thoughtfully converted from a historic mill. Downstairs, you’ll find an outpost of Batson River Brewing and Distilling, making it easy to wind down with a locally brewed beer or cocktail without ever leaving the building.

Do this: Wander through Biddeford’s revitalized historic mill district and follow the RiverWalk, where scenic views of the Saco River meet a growing collection of creative businesses housed in repurposed industrial spaces. Before you head out, leave time for some standout specialty shopping: pick up exceptional Maine cheeses at Nibblesford, grab a pint of brown butter crunch ice cream from seasonal sweet spot Sweetcream Dairy, and don’t skip the blueberry-orange brioche at Edelweiss Pastry Shop.

1hr 45mins from Boston

Mystic blends maritime history with an easygoing coastal atmosphere, making it a reliable spring-through-fall escape that feels both scenic and low-effort. Centered around its historic seaport and compact village, Mystic is ideal for a weekend of waterfront strolls, good meals and low-effort sightseeing that still feels substantial.

Eat here: The Shipwright’s Daughter is a polished but approachable spot known for its thoughtful New England–driven menu and seafood-forward cooking. For something more casual, grab lunch at Mystic Seaport Galley, where classic maritime fare comes with views of the working harbor.

Stay here: The Whaler’s Inn is a centrally located boutique hotel that puts you within walking distance of the village, riverfront and shops. Its mix of historic character and modern comfort makes it an easy, well-located base for a weekend in town.

Do this: Spend a few hours at Mystic Seaport Museum, one of the country’s most immersive maritime museums, where historic ships and a carefully preserved 19th-century seafaring village make it as compelling for architecture and history enthusiasts as it is for casual visitors. Afterward, cross the Mystic River Bascule Bridge and wander the village streets, with their mix of independent shops, cafés and waterfront views.

1hr 45mins from Boston

The Cape is a no-brainer for a Boston getaway—but where to base yourself? Try the inimitable charms of Chatham, where stately homes draped in blooming hydrangeas set the scene and the compact town center delivers a concentrated hit of excellent boutiques, galleries and cafés.

Eat this: Start with dinner at The Impudent Oyster, a Cape Cod institution set inside a converted church, where classic seafood gets smart, contemporary updates and the bar buzzes late into the evening. From there, you have zero excuses not to pop into Chatham Squire for a quintessential Cape nightcap—lively, unpretentious, and exactly what you want after dinner. For a more polished but still relaxed dinner option, Del Mar Bar & Bistro delivers upscale American fare, fresh local seafood and wood-fired pizzas in a sleek, modern space.

Stay here: For classic Cape Cod luxury, Chatham Bars Inn remains the gold standard, with sweeping ocean views, manicured grounds, and iconic beach cabanas that have long defined the resort’s reputation. For a more contemporary boutique stay, Greyfinch Chatham Inn offers a thoughtfully renovated, modern coastal retreat just minutes from Chatham’s beaches, shops, and restaurants.

Do this: Get out on the water with Monomoy Island Excursions for a seal cruise along the Chatham coastline, where you’ll spot seals lounging on nearby sandbars while cruising past historic lighthouses and working harbors. Back on land, make time for a visit to the seasonal Chatham Pier Fish Market, where you can watch local fishermen unload the day’s catch—often with seals looking on from the water—and pick up ultra-fresh seafood or a classic lobster roll right at the dock.

~2 hours from Boston

Portland, Maine, beckons with a singular, compelling invitation—to eat! This vibrant coastal city is a mecca for food lovers, packed with standout restaurants at every turn. Your only challenge will be deciding where to start.

Eat here: Start with Duckfat Frites Shack and Highroller Lobster Co., then secure a reservation for a memorable Mexican brunch at Ocotillo. For a great cocktail, head to Sur Lie, or grab a counter seat for lunch at Smalls to truly eat local-style. If time (and appetite) allows, don’t miss a steaming bowl of fresh pasta from Leeward.

Stay here: AirBnB's are always a fun option in Portland, but for a more traditional hotel stay, consider The Longfellow Hotel, a chic, independently owned boutique property near Portland’s West End, just steps from Tandem Coffee Roasters. Its 48 rooms exude sophisticated charm. For something with more quirk, try The Press Hotel in the Old Port. Once home to the Portland Press Herald, the hotel proudly showcases its print heritage with newspaper-adorned walls, letterpress-inspired carpeting and vintage typewriters throughout.

Do this: When you're not eating, explore Portland’s walkable neighborhoods and waterfront—from the cobblestone streets and shops of the Old Port to the artsy East End and Munjoy Hill, where murals, cafés and sweeping Casco Bay views await. Follow the shoreline on the Eastern Promenade Trail, a scenic waterfront walk popular with locals for strolling, biking and sunset views. With more time, hop on a ferry across Casco Bay to visit Peaks Island, or take a short drive to Cape Elizabeth to see the iconic Portland Head Light, one of New England’s most recognizable lighthouses.

2hrs from Boston

Escape to Woodstock, where the village green and clapboard streets feel lifted straight from a classic New England postcard. Often cited as one of the region’s most charming small towns, Woodstock shines brightest in autumn, when peak foliage frames covered bridges and rolling hills. Beyond the leaves, expect working farms, thoughtfully curated museums, and an idyllic town center perfect for slow wandering.

Eat here: Settle in at Worthy Kitchen for farm-to-table comfort food done right, from juicy smash burgers and twice-fried chicken wings to classic sides like creamy potato salad, all backed by an excellent lineup of Vermont craft beers on tap. For a more refined night out, book a table at The Prince & The Pauper, a longtime local favorite offering intimate, French-inspired dining with a seasonal, Vermont-forward sensibility that feels especially fitting after a day of leaf-peeping.

Stay here: Book a stay at Woodstock Inn & Resort, set directly on Woodstock’s historic town green and ideal for exploring the village on foot. In addition to its prime location, the resort offers a well-regarded spa, and access to Kelly Way Gardens, the on-site farm that supplies much of the Inn’s seasonal produce.

Do this: Make time for a visit to Sugarbush Farm, a longtime local favorite known for complimentary tastings of its house-made cheeses and maple syrup. Wander the rolling farm grounds, stop by the sugarhouse, take in sweeping foliage views in season, and stock up on Vermont-made treats at the on-site farm store. 

2 hrs from Boston

Northampton strikes a rare balance between small-town charm and big cultural energy. Anchored by Smith College and fueled by a fiercely independent spirit, this walkable Pioneer Valley hub is ideal for a relaxed weekend built around shopping, music, good food and leaf-filled strolls—especially from spring through fall.

Eat here: Settle in at Woodstar Café for a casual but well-executed meal, where the all-day menu covers everything from hearty breakfasts to thoughtfully prepared lunches and dinners. For something more refined, book a table at Homestead, a longtime local favorite known for its seasonally driven menu and polished, unfussy approach to New American cooking.

Stay here: Check into Hotel Northampton, a centrally located boutique hotel that puts you steps from Main Street’s shops, cafés and music venues. The rooms are comfortable and classic, making it an easy, no-friction home base for exploring town on foot.

Do this: Spend an afternoon browsing along Main Street, where independent bookstores, vintage shops and local boutiques reward unhurried wandering. In the evening, catch a show at Academy of Music Theatre, one of the country’s oldest continuously operating theaters, which hosts an eclectic mix of concerts, comedy and touring performances. For fresh air, head just outside town to Mount Tom State Reservation for an easy hike with sweeping valley views.

1hr 30mins + 45min ferry from Boston

A short ferry ride from Woods Hole brings you straight to Martha’s Vineyard, a classic New England island escape known for its polished towns and expansive beaches. Whether you base yourself in Edgartown, Oak Bluffs or Vineyard Haven, you’ll find no shortage of things to do, from harbor walks and historic landmarks to long, sun-soaked days on postcard-perfect sand.

Eat here: For a standout dinner focused on local sourcing, book a table at State Road Restaurant, where refined American cooking is served in a warm, rustic setting that feels quintessentially Vineyard. In Edgartown, stop by the seasonal Larsen's Fish Market, a true island institution for ultra-fresh lobster, steamers and seafood straight off the boat. After dark, join the inevitable line at Back Door Donuts for the Vineyard’s most beloved late-night ritual—hot donuts that are, in fact, worth the wait.

Stay here: For that ultimate Vineyard-style luxury, The Harbor View Hotel remains one of the island’s most coveted stays, pairing harborfront views with thoughtful perks like complimentary bikes and a fleet of Mercedes-Benz vehicles to cart you around the island. For a more approachable but still well-located option, Vineyard Square Hotel & Suites offers comfortable rooms right in the heart of Edgartown, making it easy to explore shops, restaurants and the harbor on foot.

Do this: Make the trip to the Aquinnah Cliffs Overlook, where striking red clay cliffs rise dramatically above the Atlantic and sweeping ocean views stretch toward the iconic Gay Head Light. For a slower-paced way to explore, rent bikes and take advantage of the island’s extensive network of paved bike paths, which make it easy to ride between Edgartown, Oak Bluffs and Vineyard Haven without ever needing a car. Back in town, spend an afternoon browsing along Main Street, Edgartown, one of the island’s most pleasant areas for strolling, with independent boutiques, galleries, cafés and easy harbor access.

2hrs 20mins from Boston

Skip Cape traffic altogether and take the fast ferry from the Boston Seaport to Provincetown, which delivers you straight into the heart of town in about 90 minutes. From the dock, it’s an easy stroll down Commercial Street, where galleries, cafés and people-watching of the highest caliber await. Just know that Provincetown is firmly seasonal: late May through Halloween is when the town is fully alive, while the off-season is noticeably quieter, with many businesses shuttered.

Eat here: Start your trip like a Ptown pro with a bite at The Canteen, a laid-back beachfront joint where picnic tables meet harbor views. Order the cod bánh mì and a glass of frosé, then settle in to the beachy vibe. For something more polished, dinner at The Red Inn is another Ptown rite of passage, with its dimly lit dining room, menu of hearty New England classics and views over the water. At the end of the night, gather with post–bar-hopping crowds at Spiritus Pizza, where the after-hours scene is almost as satisfying as the booze-absorbing pies.

Stay here: Airbnb rentals are an especially strong option in Provincetown, where tasteful hosts tend to go above and beyond, pairing thoughtful design with amenities that genuinely elevate your stay—think great sound systems, smart lighting and small details that don’t feel accidental. If you prefer a hotel, check into AWOL, a laid-back retreat overlooking the marshes of the Province Lands that trades Commercial Street buzz for quiet nights, an inviting pool and a nightly fire pit.

Do this: Shopping and gallery hopping along Commercial Street is unmatched among New England beach towns, with local shop owners bringing an A-plus level of curation to everything they sell—so you’re almost guaranteed to head home with a true showpiece. It’s a classic for a reason: book a ride with Art’s Dune Tours for an unforgettable trip through the sweeping sand dunes, where expert guides share the history of the landscape, the Cape Cod National Seashore and the stories behind the secluded artist shacks tucked into the dunes.

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. Expect its quintessential coastal charm and invigorating sea breezes.

Eat here: Indulge your palate at Millie's Restaurant in Madaket, a beloved institution offering a West Coast–influenced take on New England cooking. For another standout meal, make time for dinner at Straight Wharf, a longtime island favorite known for polished, seafood-forward dishes served in an intimate harborfront setting. 

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 Mediterranean-inspired dishes 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 have to 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 a more traditional cultural escape, a journey west to the Berkshires delivers rolling hills, historic estates and a deep bench of classical arts institutions. Spread across small towns and scenic backroads, it’s an ideal weekend for unhurried exploration, outdoor time and performances that feel rooted in place.

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 regularly hosts pop-up events.

Stay here: Settle into the timeless charm of The Red Lion Inn, a quintessential New England property in Stockbridge with a long-standing role in the region’s cultural life. For a more contemporary stay, Prospect Berkshires offers design-forward rooms in a quieter setting, appealing to travelers who prefer a modern base while exploring the surrounding towns.

Do this: Immerse yourself in classical and modern masterworks at the Clark Art Institute in Williamstown. For a more immersive estate experience, make a stop at Naumkeag, where formal gardens and historic interiors reward slow wandering.

2hrs 30mins from Boston

There's 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 winter sports.

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 nearby 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 45mins from Boston

For a more art-forward Berkshires trip, North Adams feels like a creative outpost tucked into the northern Berkshires, where contemporary art and post-industrial grit meet wide-open mountain scenery. Smaller and more focused than the broader Berkshires region, it’s an ideal spring-through-fall escape for travelers who like their culture bold, their scenery dramatic and their weekends easy to navigate.

Eat here: Public Eat + Drink anchors the local dining scene with seasonally driven New American cooking served in a warm, understated space that matches the town’s creative energy. For something more casual, Bright Ideas Brewing pairs inventive pub-style fare with house-brewed beer in a lively setting just steps from MASS MoCA.

Stay here: Prospect Berkshires offers a polished, design-forward stay minutes from downtown, pairing contemporary rooms with a calm, residential setting. Just outside the city center, Tourists reimagines a classic roadside motel with thoughtful design, river access and a quietly social atmosphere that suits the town’s art-forward appeal.

Do this: MASS MoCA is the reason many visitors come, and for good reason. Housed in a sprawling former factory complex, the museum’s monumental galleries make it as compelling for architecture lovers as for fans of contemporary art. Outside the museum, explore nearby trails and scenic byways through the Hoosic River Valley, especially striking during foliage season.

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 Old Harbor.

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 an 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 spot serving elevated pub 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.