After an afternoon at the Berkshire Museum, grab dinner at Spice, located in the old home of the Besse-Clark Department Store in Pittsfield. The chef hails from the Four Seasons, the menu's locally sourced, and the décor is stylishly modern (exposed brick, dark wood, dim lighting), but the real scene-stealer is the ladies’ room, built inside of the original iron scrollwork elevator.
On the way to Tanglewood for a sunset recital, stop in at Truc Orient Express (3 Harris St., West Stockbridge; 413-232-4202), a gourmet Vietnamese restaurant that doubles as an art gallery and Buddhist temple set alongside the lazy Williams River. Sit in the enclosed porch and order the Happy Pancake, a crispy rice-flour crêpe stuffed with pork, followed by the best dish on the menu: a perfectly airy lemon mousse.
On the same street that Norman Rockwell immortalized in his warm and fuzzy “Stockbridge–Christmas on Main Street,” Widow Bingham’s Tavern in the Red Lion Inn is a Berkshires classic. For a truly Rockwellian experience, nab the semi-enclosed crimson booth across from the entrance bar and carve up the roasted native turkey.
Neighboring farm workers stop by Bartlett’s Orchard in Richmond as early as 8 a.m. to load up on delicious sugar cider doughnuts ($3.79 per dozen) and fresh apple cider, two staples that keep this roadside farm stand afloat until apple-picking season begins on Labor Day.