While most South County towns have been spruced up like precious antiques, Great Barrington, with as many hardware stores as chic boutiques, is like grandma’s comfortable old sofa, still too much in daily use to keep under velvet wraps. The town doesn’t deplore the few tacky commercial lots around its fringes, perhaps because they can’t detract from the handsome buildings at its core. Prime among these buildings, which include stone churches on wide Main Street and imposing Searles Castle, a former Berkshire cottage turned private academy, is the landmark Mahaiwe Theater (413/528-0100) at 14 Castle Street, all marble and gilt trim behind its marquee. Built for vaudeville, and recently restored, it still hosts frequent theater and musical theater productions.
Besides architecture and history, Great Barrington has a lot to offer hungry travelers. Fussy early-risers seeking their cappuccino and muffins, or picnickers needing the makings of a great spread will want to check out the Berkshire Coffee Roasting Company, at 286 Main Street, which serves up espresso drinks, teas, and bakery items, with the added benefit of the South County’s best let’s-hang-out atmosphere. Bev’s Homemade Ice Cream, around the corner at 5 Railroad Street, is another source of caffeine, light lunch fare, and sugar, too, by the rich and creamy coneful.
Across from Bev’s is 20 Railroad Street, the place for burgers, sandwiches, and soups; its lively bar is the closest native example of a honky-tonk.