Winchester Arts Events

Contemporary Christian Concert presented by Clean Water of Virginia

James R. Wilkins, Jr. Athletic & Events Center 3 May 2026

Sunflower Festival

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

First Friday

Old Town Winchester Walking Mall 7 Aug 2026

Bright Box Card Bazaar: An Indoor Pokemon Vendor Show

Bright Box (Winchester, VA) 9 May 2026

Peaches & Beaches Festival

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

Cole Chaney & Kyova w/ Brennan Edwards

Bright Box Theater 6 May 2026

"Hit Me 90's One More Time!" Comedy Murder Mystery Show (7PM)

Bright Box Theater 6 Jun 2026

Kids Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 27 Jun 2026

Flutterby Fairy Festival 2026

740 Merrimans Ln Winchester, VA 6 Jun 2026

Winchester, VA @ Bright Box Theater

Bright Box Theater 31 Jul 2026

Emo Night Karaoke 7/25 @ Bright Box Theater

Bright Box Theater 25 Jul 2026

Pierogies!

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 13 Jun 2026

Calendar Girls at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 23 May 2026

Fairytale on the Farm

2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 27 Jun 2026

W.O.W. - May Networking Event

The George Washington A Wyndham Grand Hotel 12 May 2026

JILL FULTON BAND @ PICCADILLY'S

Piccadilly's Public House and Restaurant 9 May 2026

Mothers & Others: Paint & Sip

302 S Loudoun Street, Winchester, VA 7 May 2026

“The Colored Patriot: The Un-Erased Story of Thomas Laws”

100 W Piccadilly St, Winchester, VA 22601-3916, United States 28 May 2026

Paint on the Farm: Flower Garden

The Homestead Farm at Fruit Hill Orchard LLC 9 May 2026

Paint on the Farm: Summer Peaches

The Homestead Farm at Fruit Hill Orchard LLC 11 Jul 2026

Paint on the Farm: Wildflowers by the River

The Homestead Farm at Fruit Hill Orchard LLC 8 Aug 2026

Paint on the Farm: Butterfly

The Homestead Farm at Fruit Hill Orchard LLC 13 Jun 2026

Winchester Meadow Celebration

Jim Barnett Park 20 Jun 2026

Paint on the Farm: Sunflowers & Bumble Bee

The Homestead Farm at Fruit Hill Orchard LLC 13 Sep 2026

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

Escutcheon Brewing Co. 14 Nov 2025

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

Bright Box Theater 22 Aug 2025