Art museums, cozy inns, and mountain trails in the Berkshires | Field Trip

In northern Massachusetts, just below the Vermont border, the Berkshires have been a four-season destination for as long as tourism has existed in America. Over the last couple of decades, greasy spoons, summer camps, and old motor lodges have given way to trendier offerings across North Adams, Lenox, and Williamstown.

The region’s recent renaissance coincides with its rise as a cultural hub — and, more recently, an escape hatch for New Yorkers and Bostonians during the pandemic. Why should they have all the fun? At roughly four hours from Philly, the Berkshires make an easy late-fall weekend trip. You may still catch a few lingering leaves, and with any luck, an early dusting of snow. Dress warm — you’ll want plenty of time outdoors.

With its low-slung, mid-century silhouette, TOURISTS Welcome almost blends into the forested landscape behind Route 2. That’s intentional, since this property (reborn in 2018 from a 1960s motor lodge) is all about the outdoors, offering guided Appalachian Trail hikes, waterfall meditations, and a cinematic suspension bridge strung across the Hoosic River. Inside, Scandi-meets-rustic comfort reigns: fireplaces, worn-in leather, raw wood, and window nooks perfect for reading. It works just as well for families (skip the amaro cocktails) as it does for weekending stylists.

📍 915 State Rd., North Adams, Mass. 01247

While the picturesque landscapes bring many to the Berkshires, MASS MoCA has functioned as the area’s other magnet since its debut in 1999. Located in a former industrial mill complex, it’s one of the most lauded contemporary visual art museums in the country, filled with (and sometimes seemingly constructed from) colossal installations you can literally get lost in. Don’t miss the immersive light works by James Turrell.

📍 1040 Mass MoCA Way, North Adams, Mass. 01247

Just a short walk from MASS MoCA, Steeple City Social lures visitors with the scent of cinnamon and coffee — and a menu that runs from thick biscuit sandwiches and sticky buns to savory cheddar-and-pickle scones. The pies by the slice are excellent, and a rotating selection of vintage housewares lines one wall. At night, the café shifts to spritzy cocktails and potatoes with caviar dip.

📍 5 Eagle St., North Adams, Mass. 01247

Not to be outdone by MASS MoCA, the Clark Institute is the other destination museum of the Berkshires, with a collection of American and English art that includes a striking bronze cast of Degas’ Little Dancer. But the real magic — especially for families — lies outside. Its 140-acre sculpture park is free, filled with meadows, storybook woods, and walking trails that are especially enchanting with a little snow on the ground. The museum provides snowshoes.

📍 225 South St., Williamstown, Mass. 01267

Pop a bottle of sour quince, crabapple-and-McIntosh pét-nat, sparkling rosé, or one of the other exciting ciders at Berkshire Cider Project. The young cidery’s tasting room is open on Saturdays and Sundays at Greylock WORKS, a former textile mill-turned-artisan hive.

📍 508 State Rd., North Adams, Mass. 01247

A Relax & Renew day pass at Miraval Berkshires — a nationally respected spa retreat in Lenox — isn’t cheap ($509 Sundays–Fridays; $539 Saturdays). But it includes $230 in credits for treatments (mineral body peels, birch-and-juniper foot massages), fee-based activities (falconry, golf), scheduled classes (yoga, rock climbing), full access to spa amenities, lunch, and gratuities. You can easily spend the entire day here. Consider it an early holiday gift to yourself.

📍 55 Lee Rd., Lenox, Mass. 01240

If you love a cozy pub, you’ll love Water Street Grill. Historic building? Check. Friendly hospitality that makes you feel like a regular? Check. Creamy clam chowder you’d be happy to drown in? Check. At WSG, which lives in a wood-clad, century-old building, the 21 taps spout craft beers from here and away, the wings wear eight different sauces, and the meatloaf comes smothered in bourbon-kissed mushroom gravy.

📍 123 Water St., Williamstown, Mass. 01267