Winchester Christmas Events

Winchester Winter Village

Old Town Winchester Walking Mall 6 Dec 2025

Victory Christmas Bazaar

2870 Middle Road, Winchester, VA 22 Nov 2025

Winter Wonderland Christmas Market

Millwood Station Banquet Hall 22 Nov 2025

Yuletide Mystical Market

Raven Conjure 14 Dec 2025

Yule Luna Market 2025

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

Holiday Market & Big Schloss Release Day!

320 N Cameron St, Winchester, VA 29 Nov 2025

Holiday Wreath Making Workshop

The Homestead Farm at Fruit Hill Orchard LLC 13 Dec 2025

A Christmas Carol at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 7 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 29 Nov 2025

Christmas Maker’s Market

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

A Christmas Carol

Winchester Little Theatre 6 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 28 Nov 2025

Follow The Star 2025 - Live Nativity Walking Tour

Fellowship Bible Church 6 Dec 2025

A DIVA's Christmas Special

Bright Box (Winchester, VA) 20 Dec 2025

Library Shop Sale @ Handley Library

100 W Piccadilly St, Winchester, VA, United States, Virginia 22601 29 Nov 2025

Winchester Holiday Lights Trolley Tour

1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601 12 Dec 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

Legacy Christian Academy Christmas Concert

Daniel Morgan Middle School 16 Dec 2025

Christmas Market @ The Ivy Room

The Ivy Room 29 Nov 2025

Pictures with Santa @ West Oaks

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

Winterfest Open House

302 S Loudoun Street, Winchester, VA 8 Dec 2025

Christmas Tree Lighting

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 6 Dec 2025

Christmas Carol Sing

Relational Estate & Elder Law 28 Nov 2025

Holiday Concert: Yesterday Swing Orchestra

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

Keith Harkin Trio Christmas Show

Bright Box (Winchester, VA) 9 Dec 2025

A Christmas Carol

Grace Evangelical Lutheran Church 26 W Boscawen St A-201, Winchester, VA 22601 14 Dec 2025

Classic French Holiday Dinner

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

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

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

Christmas Music Bingo

4305 Middle Road, Winchester, VA, United States, Virginia 22602 17 Dec 2025

Heir and a Parent: Christmas Cookie House

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

Tree of Remembrance Ceremony (In Memory of Lives Lost to Violence)

Church of the Good Shepherd 6 Dec 2025

Northside Pro Shop Christmas Masters

Northside Lanes 21 Dec 2025

W.O.W. - Women of Winchester Christmas Jingle & Mingle

The George Washington A Wyndham Grand Hotel 9 Dec 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 20 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 23 Nov 2025

Gallery Explorers: Winter Landscape Holiday Cards

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

Holiday Wreath Making Workshop

The Homestead Farm at Fruit Hill Orchard LLC 7 Dec 2025

Heir and a Parent: Holiday Cookie Tree

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

Winter Solstice Market at Winter Village

125 S. Loudoun Street, Winchester, VA 6 Dec 2025

Black Friday at Real Deals!

381 Millwood Avenue , Winchester, VA, United States, Virginia 22601 28 Nov 2025

Four Color Fantasies Pre-Christmas Sale!

80 Weems Ln, Winchester, VA, United States, Virginia 22601 6 Dec 2025

Light the World

399 Apple Pie Ridge Rd, Winchester, VA, United States, Virginia 22603 12 Dec 2025

Christmas Tree Farm Minis

Moose Apple Christmas Tree Farm 6 Dec 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