Winchester Arts Events

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 12 Sep 2026

First Friday

Old Town Winchester Walking Mall 7 Aug 2026

The All-American Pig & Pour

302 S Loudoun Street, Winchester, VA 18 Jul 2026

Peaches & Beaches Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 1 Aug 2026

Celebracion of Winchester

Taylor Pavilion Winchester 19 Sep 2026

Live Music with John D. Neal

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 11 Jul 2026

Winchester, VA @ Bright Box Theater

Bright Box Theater 31 Jul 2026

MSV at Night: Sweet Mountain Laurel

901 Amherst St, Winchester, VA, United States, Virginia 22601 24 Jul 2026

Prohibition Party w/ Blair Crimmins + the Hookers

Bright Box Theater 31 Jul 2026

James and the Giant Peach Jr.

Winchester Little Theatre 18 Jul 2026

July TalkWALK Community Walk - Historic Winchester

Rouss City Hall 20 Jul 2026

James and the Giant Peach Jr. - WLT For Kids at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 18 Jul 2026

Valerie Smith - Maggie's Journal Historical Musical

Patsy Cline Theatre 1 Aug 2026

Honky Tonk Social at Hopscotch Coffee & Records

Hopscotch Coffee & Records 12 Jul 2026

Celebration America!

325 W. Boscawen St, Winchester, VA, United States, Virginia 22601 3 Jul 2026

Summer Open Mic Night!!!

124 W Piccadilly St, Winchester, VA 22601-3916, United States 3 Jul 2026

Wellness Walk at the Museum of the Shenandoah Valley

Museum of the Shenandoah Valley 15 Jul 2026

Blue Sky Puppets: Chester's Magic Shovel @ Handley Library!

100 W Piccadilly St, Winchester, VA, United States, Virginia 22601 21 Jul 2026

JILL FULTON BAND @ PICCADILLY'S

Piccadilly's Public House and Restaurant 11 Jul 2026

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

Escutcheon Brewing Co. 14 Nov 2025

Art Camp "Fibers Art" Ages 9-15

Easely Created Winchester 20 Jul 2026

Teen Art Club: Revolutionary Valley

901 Amherst St, Winchester, VA, United States, Virginia 22601 9 Jul 2026

Cozy Writing Workshop

124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601 20 Jun 2026

Art Camp "Pixar Art" Ages 6-14

Easely Created Winchester 13 Jul 2026

Memories at the MSV: Portraits

901 Amherst St, Winchester, VA, United States, Virginia 22601 16 Jul 2026

TWO-DAY MINI-INTENSIVE CRANIOSACRAL THERAPY PROGRAM

2654 Valley Ave, Suite A, Winchester, VA, United States, Virginia 22601 25 Jul 2026

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

Bright Box Theater 22 Aug 2025