Woodstock Playhouse
Woodstock Playhouse runs summer musicals and plays in Robert Elwyn's 1938 experiment. It burned in 1988 and rebuilt with the original facade.
The Woodstock Playhouse runs summers on programming that made small-town theater work in 1938 and still does now: musicals and plays with pre-Broadway casts, running Friday and Saturday nights at 7:30 and Sunday matinees at 2. The 2026 lineup opens with West Side Story in June, moves through Disney's Newsies in July, Theatre for Young Audiences' Alice in Wonderland, and The Play That Goes Wrong, then closes the main season with Crazy for You in August, right before the Playhouse hosts its Fingerstyle Guitar Festival August 28-30. Buy ahead for anything with a recognizable title; the house is small enough that popular shows sell out fast.
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