8 Great Weekend Getaways in New England

Are you a patron of the arts? If so, western Massachusetts’s bucolic Berkshire Mountains are sure to get your creative juices flowing. They worked for Norman Rockwell, who lived in the town of Stockbridge for 25 years—his namesake museum houses nearly 1,000 original paintings and drawings—and Herman Melville, whose restored home and farm Arrowhead is open daily for tours. In Lenox, the fin-de-siècle mansion that inspired the author and his peers is now Wheatleigh, a gracious boutique hotel on grounds designed by Frederick Law Olmsted. Drop your bags, then head to Great Barrington, a quaint town with picturesque shops (spring for the homespun ceramics and grain-sack linens at One Mercantile) and restaurants worth making the trip for (the seasonal dishes at The Prairie Whale are a must).

Though Massachusetts seems to have cornered the market on the quintessential summer by the sea, Maine’s coastal villages are worth a second look. Case in point: Kennebunkport, with its postcard-perfect lighthouses and wide swaths of sand (we’re partial to Goose Rocks Beach). You’ll find seafood worth writing home about at The Clam Shack, where there’s almost always a queue of locals and visitors waiting for hand-torn lobster rolls doused in butter and mayo. Work off those calories on a bike ride to the fishing village of Cape Porpoise, then bed down at Hidden Pond, a collection of 20 cottages with bead-board walls and woodland accents nestled among birch and balsam trees. And don’t arrive before making a reservation at Earth, which serves local, seasonal dishes made with ingredients from two on-site organic farms.

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Gilmore Girls fans need no introduction to Washington, the Connecticut town that was the inspiration for Stars Hollow. While you won’t see the real-life version of Lorelai’s Dragonfly Inn, you will find Grace Mayflower Inn & Spa, a 1900s schoolhouse that has been converted into 30 elegant rooms with four-poster beds and Frette linens. It’s an ideal base for exploring downtown’s shops and restaurants, including The Hickory Stick Bookshop and G.W. Tavern, a colonial-style brunch spot that overlooks babbling Bee Brook. Looking for something more portable? The Pantry’s to-go sandwiches, salads, and charcuterie have all the makings of a perfect pond-side picnic lunch after a hike through Mount Tom State Park. Just be sure to make a slight detour to visit Jeffrey Tillou Antiques in nearby Litchfield to pick up mint-condition brass candlesticks and 19th-century portraits.

While most tourists flock to summer like a Vanderbilt in the mansions and wharfs of Newport, locals know the real place to be is an hour’s ferry ride away, in Block Island. Base your stay at Hotel Manisses, a Victorian building turned restaurant and boutique hotel whose 17 classic rooms feature cane-backed headboards and claw foot tubs. Though it overlooks popular Ballard Beach, body surfers and boogie boarders make the 20-minute bike ride to catch the waves at Mansion Beach—with a pit stop at Dead Eye Dick’s for oysters with a harbor view. Cycling in the other direction will take you to the Gothic Revival Southeast Light, one of the country’s most architecturally savvy, and nearby Rodman’s Hollow, a 230-acre sanctuary for hawks, deer, and other coastal wildlife.

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Burlington has long been the Green Mountain State’s hippiest locale, but there’s more to this Lake Champlain town than Phish and Ben & Jerry’s. The minimalist rooms at Hotel Vermont have all the hallmarks of a hipster haven, from locally quarried granite and bath products, coffee mugs, and throw blankets by area artisans. Drop your bags, then head to pedestrian-friendly Church St. Marketplace, where Taco Gordo churns out West Coast–style carnitas and lengua on house-made corn tortillas. Thirsty? Foam Brewers has been hailed as one of the best new breweries in the world thanks to its experimental sours and IPAs—all served on a charming waterfront patio. If you’re looking for something more formal, opt for the seasonal farm-to-table dishes and craft cocktails at Hen of the Wood.

You’d be hard pressed to find a more picturesque New England town than Camden, a sleepy retreat on the Penobscot Bay with cheerful clapboard storefronts and a classic white-steeple church. Start your journey at Whitehall, an 1834 sea captain’s home that has been given new life with quirky wallpaper and colorful contemporary accents, then work up an appetite hiking to the top of Mount Battie in Camden Hills State Park. (The view of Camden Harbor is what Instagram feeds are made for.) The hotel’s Pig + Poet restaurant is the place for happy hour sundowners and fresh-shucked oysters with passionfruit mignonette, but if the siren song of something more exotic calls, beeline to Long Grain, a surprisingly authentic Thai restaurant that’s known throughout the region for its spectacular house-made noodles.

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Lake Winnipesaukee may get all the glory, but what neighboring—not to mention much smaller—Squam Lake lacks in notoriety it makes up for in simple pleasures, namely kayaking, hiking, and swimming without the crowds in the heart of New Hampshire’s pristine Lakes Region. There’s no better place to take it all in than from the family-owned Squam Lake Inn, a laid-back bed and breakfast in a refurbished 1895 farmhouse with all the modern necessities (WiFi, luxe linens, organic bath products). If you’ve had enough sun worshipping, consider enrolling in a cooking class nearby at The Manor on Golden Pond, an English country–style former artists’ colony that was also the backdrop for Katharine Hepburn and Henry Fonda in On Golden Pond.

Just 45 minutes north of Boston, Newburyport feels like another world. Though the 17th-century architecture has been updated with shops and restaurants, an old world charm remains in the former port town—you can learn about its history at the Custom House Maritime Museum. Be sure to line up at Buttermilk Baking Company before their famous peach muffins sell out, then head over to Plum Island, 10 minutes away, to laze by the shore or track birds and butterflies on the Hellcat Marsh Loop Trail. You’ll want to linger for dinner: Brine lives up to its name with fresh oysters and crudo in a lively industrial-chic setting. If the modern rooms at Blue Inn on the Beach don’t coax you into an overnight stay, the gracious suites at Newburyport’s Federal-style Compass Rose Inn surely will.