Tick off all the boxes on your iconic New England checklist: rolling farmland, pristine lakes, maple sugaring, mountain ranges. And, also, cultural hub: The Berkshires is known for its incredible roster of dance, music, and performing arts centers. 

WHERE TO STAY

The Old Inn on the Green
Red Lion Inn
Cranwell Resort & Spa
The Porches Inn at Mass MoCA

WHERE TO EAT

Allium
Haven
Nudel
Old Inn on the Green
Southfield Store

WHAT TO DO

Jacob's Pillow, a beloved cultural campus. Dance classes in the morning, lectures, free shows, evening performances, a restaurant, and a bar.
Barrington Stage Co., a non-profit performing classics (South Pacific, West Side Story) and premieres in a 1912 vaudeveille theater.
The Berkshire Fringe, summer theater festival showcasing avant garde work.
Mass MoCA, museum and performance space for contemporary works.
Canyon Ranch, a serene health spaand resort.
Shakespeare & Company, a 30-acre compound celebrating, teaching, and preserving the works of Shakespeare. Summer brings a jam-packed schedule of performances.
Downhill skiing (Butternut, Catamount)
Skinny dipping (Buckley Dunton Lake)
Bartholomew's Cobble, for a romp in the woods.
Kripalu Center for Yoga and Health, for a good stretch.

WHERE TO SHOP

Bizalions Fine Food, artisanal food stuffs.
Brimfield, site of enormous (superlative) flea market for six days in May, July, and September.
Germain, a spacious home store filled with industrial furnishings, minimalist pottery, and clothing.
Painted Porch, an antiques shop in Sheffield.
Metropolitan French Antiques, vintagey goods in Great Barrington (631 Main Street).
Rubiner's, a gourmet food shop and cheesemonger.

LOCAL COLOR

@ArtsPittsfield
Berkshares (local currency!)
Berkshire Creative
Berkshire Eagle
Rural Intelligence
WAMC
Berkshireradio