Winchester Holiday Events

Holiday events Happening Next in Winchester, VA

Yuletide Mystical Market

 Raven Conjure 7 Dec 2025
HOLIDAY

Holiday Market & Big Schloss Release Day!

 320 N Cameron St, Winchester, VA 29 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS

A Christmas Carol

 Winchester Little Theatre 6 Nov 2025
CHRISTMAS-CAROLS

Celebracion of Winchester

Taylor Pavilion Winchester 20 Sep 2025
KIDS

Yule Luna Market 2025

 125 S. Loudoun Street, Winchester, VA 29 Nov 2025
HOLIDAY

Dancing Thru the Decades

 Backseat Events 7 Feb 2026
FESTIVALS

The Faire at Canterbury

 300 Westminster Canterbury Drive, Winchester, VA, United States, Virginia 22603 20 Sep 2025
PERFORMANCES

2025 Winchester Medical Center NICU Reunion

 West Oaks Farm Market 12 Oct 2025
KARAOKE

Breaking Breads

 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 15 Nov 2025
WORKSHOPS

Winchester Winter Village

 Old Town Winchester Walking Mall 6 Dec 2025
KIDS

A Christmas Carol at Winchester Little Theatre Inc.

 Winchester Little Theatre Inc. 7 Nov 2025
ART

Karaoke Night with Route 11 DJ

 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 21 Nov 2025
KARAOKE

A Christmas Carol at Winchester Little Theatre

 Winchester Little Theatre 23 Nov 2025
ART

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

 102 Montague Ave 7 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS FREE

2025 Shenandoah Potters Guild Annual Holiday Pottery Show & Sale

 1460 University Dr, Winchester, VA 22601, United States 29 Nov 2025
HOLIDAY

SPCA Thrift Black Friday Blowout - November 28th

 1944 Abrams Creek, Winchester, VA, United States, Virginia 22601 28 Nov 2025
BLACK-FRIDAY

Community Meeting: Celebrating the Seasons: Holiday Events in Old Town

 Winchester Brew Works 20 Aug 2025
MEETUPS

Bring Your Own Gingerbread House- Gingerbread Making Contest!

 320 N Cameron St, Winchester, VA 18 Dec 2025
CONTESTS