Your Guide to the Berkshires' Best
Food, adventures, arts, culture — everything you need for the most memorable Berkshire vacation, all in one place.
Let us help you have the most fun, relaxing, delicious, and memorable trip.
Where to Eat
From farm-to-table dining to morning coffee rituals, the Berkshires' food scene punches well above its weight. Here are the spots we keep coming back to.
Food & Drink
The Prairie Whale
Farm-driven dishes in a warm, rustic setting — one of the region's best dinners.
The Old Inn On The Green
Candlelit prix-fixe dining in a historic 18th-century inn. Truly special.
Guido's Fresh Marketplace
The go-to stop for gourmet groceries, prepared foods, and local produce in Great Barrington and Pittsfield.
Six Depot Roastery & Cafe
Specialty coffee roasted on-site in a converted train depot. The morning ritual.
Alta
Wine bar and small plates with a sophisticated, seasonal menu.
Berkshire Mountain Bakery
Wood-fired sourdough pizza and legendary bread — a Berkshires institution.
What To Do
Ski runs in winter, wildflower hikes in spring, lake swims in summer, foliage walks in fall. The Berkshires are an outdoor playground year-round.
Outdoor Adventures
Jiminy Peak Mountain Resort
Skiing, snowboarding, and a mountain coaster — the region's premier ski destination.
Olivia's Overlook
A short hike to one of the most breathtaking panoramic views in the Berkshires.
Berkshire Botanical Garden
Fifteen acres of gardens, woodland trails, and seasonal events in Stockbridge.
Catamount Aerial Adventure Park
Ziplines, rope bridges, and treetop courses for the adventurous at heart.
Pleasant Valley Wildlife Sanctuary
Mass Audubon's sanctuary with beaver ponds, meadows, and miles of quiet trails.
Mount Greylock
Year-round outdoor activities, featuring hiking, camping, and scenic drives to the state's highest peak.
The Creative Heart
Tanglewood. Shakespeare & Company. MASS MoCA. Norman Rockwell. The Berkshires have been a cultural destination for over a century — and the tradition is only getting richer.
Arts & Culture
Tanglewood
The summer home of the Boston Symphony Orchestra. Picnic on the lawn, music under the stars.
Shakespeare & Company
World-class theater in Lenox — from the Bard to bold new works, get your tickets now.
MASS MoCA
One of the largest contemporary art museums in the country, housed in a sprawling former factory in North Adams.
Norman Rockwell Museum
The definitive collection of America's most beloved illustrator, right here in Stockbridge.
The Mount — Edith Wharton's Home
Tour the stunning estate of the Pulitzer Prize-winning author, with gardens, lectures, and seasonal events.
Mahaiwe Performing Arts Center
Live music, film, dance, and community events in a beautifully restored 1905 theater in Great Barrington.
