Winchester Arts Events

Sunflower Festival

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

First Friday

Old Town Winchester Walking Mall 7 Aug 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

Prohibition Party w/ Blair Crimmins + the Hookers & The Hot Mamas

Bright Box Theater 31 Jul 2026

Winchester, VA @ Bright Box Theater

Bright Box Theater 31 Jul 2026

Playground Pop–Up

1001 E Cork St, Winchester, VA, United States, Virginia 22601 30 Jul 2026

GIRLY POP

Bright Box Theater 21 Aug 2026

Maggie's Journal Concert featuring Valerie Smith

John Handley High School 1 Aug 2026

Farm Concert- Chad Laughlin & Riley Kerns

4305 Middle Road, Winchester, VA, United States, Virginia 22602 14 Aug 2026

Youth Initiative: Type Writer Studio Youth Watercolor Workshop

The Typewriter Studio 10 Aug 2026

Andrew Renner Live at the Half Note Lounge

103 E Piccadilly St, Winchester, VA, United States, Virginia 22601 31 Jul 2026

Valerie Smith - Maggie's Journal Historical Musical

Patsy Cline Theatre 1 Aug 2026

Third Battle of Winchester 162nd Anniversary Tours

Third Winchester Battlefield Park 19 Sep 2026

Watercolor Painting Class "Floral Wreaths" at Easely Created

Easely Created Winchester 1 Aug 2026

2nd Annual Community Picnic

Willow Grove Farm 30 Aug 2026

Inaugural Kernstown Battlefield Tour of New Sandy Ridge Connector Trail

Rose Hill Park 31 Jul 2026

The Long Ash Bash

141 featherbed ln, Winchester, VA 12 Sep 2026

Roaring 20's Prohibition Party

15 N Loudon St. Winchester, VA 22601 31 Jul 2026

"Savings Saturday" $25 Paint Class 16x20 Canvas at Easely Created

Easely Created Winchester 22 Aug 2026

"Happy Cappy" Creative Kids Paint Class Ages 6-14 at Easely Created

Easely Created Winchester 22 Aug 2026

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

Escutcheon Brewing Co. 14 Nov 2025

Author Jerry Ankeny - Somerset County, Pennsylvania’s soldiers at Hupp’s Hill and Cedar Creek

Shenandoah Valley Civil War Museum 24 Oct 2026

November HOMESCHOOL ART at Easely Created

Easely Created Winchester 10 Nov 2026

Cozy Writing Workshop

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

Summer Art Classes at The YDC!

302 S Loudoun Street, Winchester, VA 8 Jul 2026

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

Bright Box Theater 22 Aug 2025

September HOMESCHOOL ART at Easely Created

Easely Created Winchester 8 Sep 2026

December HOMESCHOOL ART at Easely Created

Easely Created Winchester 8 Dec 2026