Great Barrington is a small town that punches well above its size in terms of culture and outdoor recreation. The surrounding Berkshires offer serious hiking — the Appalachian Trail passes nearby — and the town itself has an unusually good collection of galleries, antique shops, and live music venues for a place with fewer than 8,000 residents. The cultural calendar fills up in summer when Tanglewood (nearby in Lenox) draws visitors from Boston and New York.