When you’re in the mood for high-quality cultural entertainment, nothing short of an evening at the theatre, a slow walk through a museum, or an open-minded crawl through an art gallery will do. In Winchester; you can take your choice.
ENTERTAIN YOUR RIGHT BRAIN
ART GALLERIES
A bevy of art galleries – both upscale and down-to-earth – hang shingles within the shopping venues in the area. The Eugene B. Smith Gallery represents one of Winchester’s most popular artists. Smith’s dreamy watercolors are collected internationally and often depict the changing landscapes and building-scapes in and around Winchester.
MAGIC LANTERN THEATRE
A non-profit community art theatre project, each year the slate of Magic Lantern films includes critically acclaimed “indie” films that didn’t make it to Winchester’s commercial theaters. The movies are aired in various settings throughout Winchester – at the regional library, at local churches, at a nearby vineyard. In the summer months, the theatre hosts a block party of sorts when it takes the movie experience outdoors in places like Indian Alley.
MUSEUM OF THE SHENANDOAH VALLEY
Some consider the pièce de résistance for the culturally minded to be the Museum of the Shenandoah Valley, designed by world-famous architect Michael Graves. The museum and its stately Glen Burnie House and Gardens showcase the area’s rich history through art, artifacts, antiques, and unique decorative objects from the Shenandoah Valley – and, most important, they share the stories that go with them.
MUSICA VIVA
Winchester’s independent chamber choir, Musica Viva, performs a diverse repertoire of fine choral literature throughout Virginia and along the East Coast.
SHENANDOAH PERFORMS
An annual program of high-caliber, professional-level performances hosted by Shenandoah Conservatory, a respected school of music, theatre, and dance that’s part of Shenandoah University.
SHENANDOAH SUMMER MUSIC THEATRE
The summer theatre is hosted by Shenandoah University and performs in the school’s Ohrstrom-Bryant Theatre. Each of its four summer shows features a full chorus and a live orchestra.
WAYSIDE THEATRE
A professional theatre operating out of a revitalized historic building in Middletown, is the second oldest community theatre in Virginia. Each year, the theatre company offers a slate of live productions that attracts distinguished actors and other professionals from across the nation, including New York, Chicago, Atlanta, and Washington, D.C.
WINCHESTER LITTLE THEATRE
An entirely volunteer-driven community theatre that produces four plays each year. Its performances take place in a charming 1890s Pennsylvania Railroad freight station in downtown Winchester. Ever the pioneers, the organizers of the Winchester Little Theatre have launched the troupe’s first experimental “24-hour theatre.” At a rip-roaring pace, the auditions kick off on a Friday evening, followed by original playwriting and rehearsal during the day on Saturday and the performance on Saturday night.
WINCHESTER ORCHESTRA
An innovative professional chamber orchestra composed of musicians whom also perform with the likes of the National Symphony, Wolf Trap Opera, Maryland Symphony, and Fairfax Symphony, to name a few.






