The Woodstock Opera House was built in 1890 to house City Hall, the public library, the fire department and an auditorium. The Opera House has been at the core of community service in the area since its construction.

In 1947, a group of citizens formed and supported the Woodstock Players. The Woodstock Players provided acting experience for students graduating from the Goodman School. Now-famous personalities such as Paul Newman, Tom Bosley, Betsy Palmer, Geraldine Page, Shelley Berman and Lois Nettleton were among them.

The venue is still home to community theater, opera and the occasional touring production.