Thanks to a May, 2015 article in the NY Times, I stopped in Great Barrington. This is a small town in the Berkshires south of Lenox and Stockbridge. It has a charming downtown area with a number of boutiques and restaurants along Main St. and Railroad St.
Make sure to check out:
Fuel Coffee Shop: At 286 Main St., this a cozy spot for coffee, tea, pastries and other food items.
Patisserie Lenox: I really enjoyed their Hudson, NY location for lunch. This is an equally attractive shop at 313 Main St. in Great Barrington. They have lovely pastries and tarts plus serve coffee, tea and lunch and breakfast items.
Conde Nast Traveler in 10/15 described it as one of the three best small-town food scenes in America and recommended Prairie Whale at 178 Main St. for locally-sourced American fare and cocktails.
Mahaiwe Performing Arts Center in Great Barrington: Located in a renovated theater from 1905, the Mahaiwe is now a unique year-round performing arts center presenting music, dance, theater, opera, and classic films in the southern Berkshires.