Winchester Holiday Events

Holiday events Happening Next in Winchester, VA

A Christmas Carol

 Winchester Little Theatre 6 Nov 2025
CHRISTMAS-CAROLS

Holiday Market & Big Schloss Release Day!

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

Yuletide Mystical Market

 Raven Conjure 7 Dec 2025
HOLIDAY

Celebracion of Winchester

Taylor Pavilion Winchester 20 Sep 2025
KIDS

A Christmas Carol at Winchester Little Theatre

 Winchester Little Theatre 29 Nov 2025
ART

Christmas Maker’s Market

2502 N. Frederick Pike, Winchester, VA 6 Dec 2025
HOLIDAY

Harvest Pumpkin Fall Centerpiece Workshop

 The Homestead Farm at Fruit Hill Orchard LLC 1 Nov 2025
WORKSHOPS USD 82

The Faire at Canterbury

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

Winchester Winter Village

 Old Town Winchester Walking Mall 6 Dec 2025
KIDS

2025 Winchester Medical Center NICU Reunion

 West Oaks Farm Market 12 Oct 2025
KARAOKE

Gallery Explorers: Winter Landscape Holiday Cards

 901 Amherst St, Winchester, VA, United States, Virginia 22601 15 Nov 2025
HOLIDAY

Yule Luna Market 2025

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

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

Cake It 'Til You Make It: A beginners guide to cake decorating

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

Dancing Thru the Decades

 Backseat Events 7 Feb 2026
FESTIVALS

Holiday Wreath Sale

 901 Amherst St, Winchester, VA, United States, Virginia 22601 1 Nov 2025
HOLIDAY

A Christmas Carol at Winchester Little Theatre

 Winchester Little Theatre 23 Nov 2025
ART

Breaking Breads

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

Family Luminary

 314 Hope Dr, Winchester, VA 22601-6800, United States 3 Dec 2025
HOLIDAY

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

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

Museum Store Sunday

 901 Amherst St, Winchester, VA, United States, Virginia 22601 30 Nov 2025
SHOPPING

Holiday Concert: Yesterday Swing Orchestra

 901 Amherst St, Winchester, VA, United States, Virginia 22601 14 Dec 2025
MUSIC

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

Holiday Tea

 901 Amherst St, Winchester, VA, United States, Virginia 22601 9 Dec 2025
HOLIDAY

Bring Your Own Gingerbread House- Gingerbread Making Contest!

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

Adult Workshop: Woven Ornaments

 901 Amherst St, Winchester, VA, United States, Virginia 22601 6 Dec 2025
WORKSHOPS

Adult Workshop: Woven Ornaments

 901 Amherst St, Winchester, VA, United States, Virginia 22601 6 Dec 2025
WORKSHOPS

Holiday Bluegrass Concert: Jack Dunlap

 901 Amherst St, Winchester, VA, United States, Virginia 22601 7 Dec 2025
CONCERTS