Winchester Arts Events

Arts events Happening Next in Winchester, VA

Sunflower Festival

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

First Friday

 Old Town Winchester Walking Mall 7 Aug 2026
OPEN-MIC

Peaches & Beaches Festival

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

Flutterby Fairy Festival 2026

 740 Merrimans Ln Winchester, VA 6 Jun 2026
FESTIVALS

Kids Festival

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

Celebracion of Winchester

Taylor Pavilion Winchester 19 Sep 2026
KIDS

ARE R.I.S.E Center's Inaugural Queer Book Fair

 124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601 13 Jun 2026
ART

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

 Bright Box Theater 6 Jun 2026
COMEDY

Calendar Girls at Winchester Little Theatre Inc.

 Winchester Little Theatre Inc. 23 May 2026
ART

Winchester, VA @ Bright Box Theater

 Bright Box Theater 31 Jul 2026
PARTIES

Date Night Sip&Paint

 16 S Loudoun St 12 Jun 2026
ART USD 34

Pierogies!

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

Emo Night Karaoke 7/25 @ Bright Box Theater

 Bright Box Theater 25 Jul 2026
KARAOKE USD 20

Fairytale on the Farm

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

Comedy to the Rescue

 15 N Loudoun St, Winchester, VA 22601-4715, United States 23 Jun 2026
COMEDY

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

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

Welcome Summer! Lunch N' Bid Fundraiser

 The George Washington Hotel 28 Jun 2026
NONPROFIT

Design & Build Dashboard | Tableau Certification in Winchester, VA

 Regus Center 26 May 2026
WORKSHOPS USD 1,587 TO 2,075

Paint on the Farm: Wildflowers by the River

 The Homestead Farm at Fruit Hill Orchard LLC 8 Aug 2026
ART USD 60

Paint on the Farm: Summer Peaches

 The Homestead Farm at Fruit Hill Orchard LLC 11 Jul 2026
ART USD 60

Paint on the Farm: Butterfly

 The Homestead Farm at Fruit Hill Orchard LLC 14 Jun 2026
FITNESS USD 60

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

 Escutcheon Brewing Co. 14 Nov 2025
COMEDY USD 13

Winchester Meadow Celebration

 Jim Barnett Park 20 Jun 2026
WORKSHOPS

Paint on the Farm: Sunflowers & Bumble Bee

 The Homestead Farm at Fruit Hill Orchard LLC 13 Sep 2026
ART USD 75

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

 Bright Box Theater 22 Aug 2025
BINGO FREE