Winchester Holiday Events

Yule Luna Market 2025

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

Yuletide Mystical Market

Raven Conjure 14 Dec 2025

Breaking Breads

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

Holiday Market & Big Schloss Release Day!

320 N Cameron St, Winchester, VA 29 Nov 2025

A Christmas Carol

Winchester Little Theatre 6 Nov 2025

Winchester Winter Village

Old Town Winchester Walking Mall 6 Dec 2025

Classic French Holiday Dinner

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 12 Dec 2025

Gallery Explorers: Winter Landscape Holiday Cards

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

Victory Christmas Bazaar

2870 Middle Road, Winchester, VA 22 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 20 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 16 Nov 2025

Harvest Pumpkin Fall Centerpiece Workshop

The Homestead Farm at Fruit Hill Orchard LLC 1 Nov 2025

Gallery Explorers: Winter Landscape Holiday Cards

901 Amherst St, Winchester, VA, United States, Virginia 22601 20 Dec 2025

Holiday Wreath Sale

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

West Oaks Holiday Craft Show

4305 Middle Road, Winchester, VA, United States, Virginia 22602 29 Nov 2025

Winter Wonderland Christmas Market

Millwood Station Banquet Hall 22 Nov 2025

Christmas Maker’s Market

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

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 15 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 22 Nov 2025

Gourmet Cookies

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 13 Dec 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 29 Nov 2025

Heir and a Parent: Christmas Cookie House

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 13 Dec 2025

🟣 Scout Spark: A Sister Scout’s Social

Valerie Hill Vineyard & Winery 7 Dec 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 23 Nov 2025

Museum Store Sunday

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

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

102 Montague Ave 7 Nov 2025

Family Luminary

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

A Day in the Kitchen: Advanced Macaron

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 20 Dec 2025

Teen Art Club: Holiday Crafts

901 Amherst St, Winchester, VA, United States, Virginia 22601 11 Dec 2025

Adult Workshop: Holiday Wreaths

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

Little Noon Music - Shenandoah Conservatory's Trombone Collective

100 W Piccadilly St, Winchester, VA, United States, Virginia 22601 5 Dec 2025

Gallery Explorers: Winter Landscape Holiday Cards

901 Amherst St, Winchester, VA, United States, Virginia 22601 16 Dec 2025

Holiday Concert: Yesterday Swing Orchestra

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

Heir and a Parent: Holiday Cookie Tree

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 21 Dec 2025

Pictures with Santa @ West Oaks

4305 Middle Road, Winchester, VA, United States, Virginia 22602 13 Dec 2025

2025 Shenandoah Potters Guild Annual Holiday Pottery Show & Sale

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

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 13 Nov 2025

SPCA Thrift Black Friday Blowout - November 28th

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

Holiday Tea

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

Holiday Tea

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

Holiday Bluegrass Concert: Jack Dunlap

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

Adult Workshop: Holiday Centerpiece

901 Amherst St, Winchester, VA, United States, Virginia 22601 11 Dec 2025

Adult Workshop: Woven Ornaments

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

Adult Workshop: Woven Ornaments

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

Adult Workshop: Holiday Centerpiece

901 Amherst St, Winchester, VA, United States, Virginia 22601 11 Dec 2025

Homeschool Wednesday Workshop: Holiday Ornaments

901 Amherst St, Winchester, VA, United States, Virginia 22601 3 Dec 2025