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

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

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

Kids Festival

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

Celebracion of Winchester

Taylor Pavilion Winchester 19 Sep 2026

MSV at Night: Michelle Lockey

901 Amherst St, Winchester, VA, United States, Virginia 22601 26 Jun 2026

Jeff Little Trio w/ Reno & Dunlap Bluegrass

Bright Box Theater 27 Jun 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

Acoustic Music at MSV Music Nights

Museum of the Shenandoah Valley 26 Jun 2026

IMPROV COMEDY with Porkchop Volcano

Bright Box Theater 12 Jun 2026

Pierogies!

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

Date Night Sip&Paint

16 S Loudoun St 12 Jun 2026

Fairytale on the Farm

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

Comedy to the Rescue

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

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

Winchester Little Theatre Inc. 18 Jul 2026

The Three Musketeers - WLT For Kids at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 20 Jun 2026

The Art of the Plate

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 23 Jun 2026

Marvelous Macaron

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 14 Jun 2026

Letterfly Pinstriping for Blue Ridge Rumble HOG Rally at Skyline Harley-Davidson

Skyline Harley-Davidson 16 Jun 2026

Welcome Summer! Lunch N' Bid Fundraiser

The George Washington Hotel 28 Jun 2026

Summer Art Classes at The YDC!

302 S Loudoun Street, Winchester, VA 3 Jun 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

Winchester Meadow Celebration

Jim Barnett Park 20 Jun 2026

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

Memories at the MSV: Art in the Drawing Room

901 Amherst St, Winchester, VA, United States, Virginia 22601 18 Jun 2026

TWO-DAY MINI-INTENSIVE CRANIOSACRAL THERAPY PROGRAM

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

Memories at the MSV: Portraits

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

Art Camp "Pixar Art" Ages 6-14

Easely Created Winchester 13 Jul 2026

Weekly SINGO Music Bingo Nights at Bright Box - Winchester

Bright Box Theater 22 Aug 2025

Coffee & Coloring

124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601 19 Jun 2026