BENNINGTON

Bennington was chartered in 1749 — the oldest chartered town in Vermont — and today its three distinct centers span Revolutionary War history, a working downtown, and a liberal arts college village.

Oldcastle Theatre Company, founded in 1972, stages productions at 331 Main Street in the heart of the downtown historic district. The company operates out of the Bennington Performing Arts Center, drawing on both professional touring talent and ties to nearby Bennington College in North Bennington.

Old Bennington holds the 306-foot Battle Monument and the 1806 Old First Church on the hill. Downtown, the Walloomsac River runs behind Main Street's brick storefronts, breweries, and antique shops. North Bennington draws artists and academics around Powers Market, open since 1833.

Tip: The downtown walking tour links Main Street's commercial blocks to the Walloomsac River walk — a useful route between dinner and showtime at the Bennington Performing Arts Center.

Neighborhoods: Downtown Bennington • Old Bennington • North Bennington