415 Braddock Street, Old Town Winchester. Wayside Theater Shenandoah's most exciting live professional theatre company with a 32 year history of producing a wide range of contemporary and classic comedies, dramas and musicals. Season runs May, October - December. Call for shows and times. The area's only petting zoo situated on approximately 5 acres.
Visitors are able to interact with the animals through petting and feeding.
Winchester Little Theater Quaint theatre comprised of local talent that offers a variety of performances each year. Housed in a former train station depot, the theatre, which holds up to 96 people, has been a part of the Winchester community for 66 years. Times and performances vary. Call Box Office for more information. Located on Boscawen Street in the heart of Old Town Winchester.