Ssssh, don’t tell anyone, but The Berkshires is the best-kept secret getaway around these parts – just two hours from Boston. We tapped our squad of elite tastemakers to share their cherished restaurants, legit (and quaint) general stores, stunning hotel estates…even arguably the world’s best hot dog.
For the Lovers…
Pucker up! You and your heart-ner are in for the ultimate romantic escape.
Where to stay: The Wheatleigh is one of the old Berkshire "cottages" that retains its old world elegance but with modern understated decor, fabulous food, incredible wine selection and unrivaled customer service. It is formal and well worth it. W Hawthorne Road, Lenox, 413-637-0610
Where to eat: Seven courses. Repeat that. SEVEN courses are waiting for you at the Old Inn on the Green, a 300-year-old inn and dining room with no electricity (but heat, thank you). Lovers dine by candlelight. 134 Hartsville-New Marlboro Road, New Marlborough, 413-229-7924
Where to shop:Karen Allen Fiber Arts (yes, the actress from “Indiana Jones” flicks) offers great women' s clothing, but the true gems are the hand loomed scarves, hats, and sweaters by Allen herself. For night time, check out Pine Cone Hill Outlet in Pittsfield for great bedding and blankets. 8 Railroad St., Great Barrington, 413-528-8555; 125 Pecks Road, Pittsfield, 800-442-8157
What to do: A romantic stroll in Kennedy park. You can get coffee or trail mix for your hike next door at the Arcadian Shop. 91 Pittsfield Road, Lenox, 413-637-3010
For the Culture Vulture
Painting, sculpture, music…The Berkshires provides inspo for your every sensory whim.
Where to stay: At the Stonover Farm, Suky & Tom Werman have created a warm, modern and comfortable Inn. Hot tip: Be sure to ask Tom to show you his office, where you’ll see the gold and platinum records of all the hard rock bands he produced in the 70s, 80s, and 90s. 169 Under Mountain Road, Lenox, 413-637-9100
Where to dine: Served on pottery that Bizen owner and chef Michael Marcus makes himself, Bizen serves up delicious sushi, country Japanese food, and organic vegetarian dishes. The Kaiseki rooms are traditional tatami, offering a transportive experience. 17 Railroad St., Great Barrington, 413-528-4343
What to do: Where to begin? There’s the Mass MOCA, featuring a world-class collection of modern art, the Norman Rockwell Museum for stunning Americana, and the Sterling and Francine Clarke Institute for the masters. MassMOCA, 87 Marshall St., North Adams, 413-662-2111; Normal Rockwell, 9 MA-183, Stockbridge, 413-298-4100; Clarke, 225 South St., Williamstown, 413-458-2303
For the Outdoorsy
From skiing to snowshoeing, there’s a rich outdoors scene in the Berkshires – and a much-appreciated “apres” culture, too.
Where to stay: With a packed winter sports itinerary, the Cranwell Spa & Golf Resort delivers the goods. Cross country ski during the day…Swedish massage at night? Yup, that’ll work. 55 Lee Road, Lenox, 413-637-1364
Where to eat: Rouge is the closest thing to "Cheers" in the Berkshires. Everyone knows your name, thanks to the lovely hostess Maggie, Chef William, bartender Jeremy and great servers like Hannah. Don’t be surprised to spot local residents including YoYo Ma and former Governor Patrick.
What to do: Skiing at Catamount, Butternut, and Jiminy Peak.
Where to shop: Athletic types translate this into buying more food. First stop, Bartlett Orchards for apple cider donuts, then it’s onto the world’s greatest baby hot dog at Teo's. Finally, pop into the West Stockbridge general store for handmade goodies. Bartlett's Orchard 575 Swamp Road, Richmond; Teo’s, 1410 East St., Pittsfield; West Stockbridge Public Market, 8 Main St., West Stockbridge, 413-232-8595