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 Performing Arts Center (14 Castle St., 413/528-0100), all marble and gilt trim behind its marquee. Built for vaudeville and recently restored, the Mahaiwe still hosts frequent film, theater, and musical theater productions.
Besides architecture, history, and a very welcome ribbon of parkland along the Housatonic River, Great Barrington has a lot to offer hungry travelers. Early-risers will want to head about a mile north of downtown on US-7 to RiverBend Cafe (401 Stockbridge Rd., 413/528-0858), which serves up espresso drinks, teas, and bakery items, with the added benefit of the South County’s best let’s-hang-out atmosphere.