Winchester Christmas Events

Winchester Winter Village

Old Town Winchester Walking Mall 6 Dec 2025

Yule Luna Market 2025

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

Yuletide Mystical Market

Raven Conjure 14 Dec 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

Holiday Wreath Sale

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

Classic French Holiday Dinner

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

Follow The Star 2025 - Live Nativity Walking Tour

Fellowship Bible Church 6 Dec 2025

Winter Wonderland Christmas Market

Millwood Station Banquet Hall 22 Nov 2025

Big Hair, Bright Lights & Spank the 80s!

114 Full House Drive, Winchester, VA 19 Dec 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 22 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 16 Nov 2025

Gingerbread Mini Sessions

Downtown Walking Mall 8 Nov 2025

Gallery Explorers: Winter Landscape Holiday Cards

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

Tree of Remembrance Ceremony (5th Annual)

Church of the Good Shepherd 6 Dec 2025

Heir and a Parent: Holiday Cookie Tree

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

Holiday Concert: Yesterday Swing Orchestra

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

🎁 2nd Annual Kids Shopping Free Event at SPCA Thrift! 🎄

1944 Abrams Creek, Winchester, VA, United States, Virginia 22601 20 Dec 2025

A Christmas Carol at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 7 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

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

Holiday Wreath Making Workshop

The Homestead Farm at Fruit Hill Orchard LLC 13 Dec 2025

Heir and a Parent: Christmas Cookie House

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

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 23 Nov 2025

WLT - Fundraiser - A Christmas Carol

315 W Boscawen St, Winchester, VA 22601-3809, United States 6 Nov 2025

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

102 Montague Ave 7 Nov 2025

Little Noon Music - Shenandoah Conservatory's Trombone Collective

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

Family Luminary

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

2025 Christmas Mini - Indoor Wreaths

The Ivy Room 9 Nov 2025

Holiday Wreath Making Workshop

The Homestead Farm at Fruit Hill Orchard LLC 7 Dec 2025

Pictures with Santa @ West Oaks

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

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 13 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

A Christmas Carol

Winchester Little Theatre Inc. 16 Nov 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

Christmas Bake Sale and Take-Out

1700 Amherst St, Winchester, VA 20 Dec 2025