26 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
First Friday in Old Town Winchester Fri 7 Aug 2026, 5:00 PM — Festival Loudoun Street Walking Mall · 127 N Loudoun St, Winchester, VA 22601 · Free
Maker Day: Clay 101 Sat 8 Aug 2026, 10:00 AM — Crafts Museum of the Shenandoah Valley Makerspace Studio · 901 Amherst St, Winchester, VA 22601 · Registration required
Yoga Mind Meetup at Please Boutique Sat 8 Aug 2026, 4:00 PM — Fitness Please Boutique · 16 S Loudoun St, Winchester, VA 22601
Experience Fusion Karaoke Sat 8 Aug 2026, 5:00 PM — Karaoke 1169 Berryville Ave · 1169 Berryville Ave, Winchester, VA 22601 · 18+
Crowded Streets: The Dave Matthews Band Experience presents Dave and Tim Sat 8 Aug 2026, 8:00 PM — Live music Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601
Author Event: Sharon Pajka Sun 9 Aug 2026, 12:00 PM — Meetup Winchester Book Gallery · 7 N Loudoun St, Winchester, VA 22601 · Free
Dalchord Fri 14 Aug 2026, 8:00 PM — Live music Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601
Author Event: C. W. Armbrust Sat 15 Aug 2026, 11:00 AM — Meetup Winchester Book Gallery · 7 N Loudoun St, Winchester, VA 22601 · Free
Robbie Fulks Sat 15 Aug 2026, 7:00 PM — Live music Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601
GIRLY POP Fri 21 Aug 2026, 8:00 PM — Live music Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601 · 21+
Dawg Days of Summer: Hot Dog Crawl Sat 22 Aug 2026, 12:00 PM — Festival Old Town Winchester Walking Mall · 127 N Loudoun St, Winchester, VA 22601
Dream Catcher Creation Class Sat 22 Aug 2026, 1:00 PM — Crafts Moon Phased · 125 S Loudoun St, Winchester, VA 22601
Tyler Booth w/ James Tamelcoff Sat 22 Aug 2026, 8:00 PM — Live music Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601
Phil Zuckerman's Summer Rock Room Concert Sun 23 Aug 2026, 1:30 PM — Live music Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601
Gallery Talk: Portraits of the Revolutionary Valley Sun 23 Aug 2026, 2:00 PM — Art show Museum of the Shenandoah Valley · 901 Amherst St, Winchester, VA 22601 · Registration required
Free Community Dance Night Wed 26 Aug 2026, 7:00 PM — Live music Vibrissa Beer · 10 N Kent St, Winchester, VA 22601 · Free · 21+
MSV at Night: Karma Creak Fri 28 Aug 2026, 5:00 PM — Live music Museum of the Shenandoah Valley · 901 Amherst St, Winchester, VA 22601 · Discounted evening ticket
Noah Guthrie w/ Tyler Nail Sun 30 Aug 2026, 6:30 PM — Live music Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601
YDC Community Flow Tue 1 Sep 2026, 5:30 PM — Fitness Youth Development Center · 302 S Loudoun St, Winchester, VA 22601
Come From Away — Selah Theatre Project Fri 11 Sep 2026, 7:00 PM — Theater 302 N Braddock St · 302 N Braddock St, Winchester, VA 22601
Standup Comedy at Escutcheon Brewing Fri 11 Sep 2026, 8:00 PM — Comedy Escutcheon Brewing Co. · 142 W Commercial St, Winchester, VA 22601 · 21+
Meet the Bees & Beekeepers Sun 13 Sep 2026, 2:00 PM — Meetup Museum of the Shenandoah Valley · 901 Amherst St, Winchester, VA 22601 · Registration required
MSV at Night: Amy Andrews Fri 18 Sep 2026, 5:00 PM — Live music Museum of the Shenandoah Valley · 901 Amherst St, Winchester, VA 22601 · Discounted evening ticket
PRIDE at the MSV Sat 3 Oct 2026, 10:00 AM — Pride Museum of the Shenandoah Valley · 901 Amherst St, Winchester, VA 22601 · Free site-wide admission
Emo Night Karaoke Sat 7 Nov 2026, 7:00 PM — Karaoke Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601 · 21+
Evening With The Babys Thu 31 Dec 2026, 8:30 PM — Live music The George Washington, A Wyndham Grand Hotel · 103 E Piccadilly St, Winchester, VA 22601 · 21+
Listings are seeded from venue and organiser calendars. See them on the map.