Holiday events in Winchester

Check out happening holiday events all around Winchester, VA

Winchester Winter Village

 Sat, 06 Dec at 11:00 am Old Town Winchester Walking Mall

Yule Luna Market 2025

 Sat, 29 Nov at 10:00 am 125 S. Loudoun Street, Winchester, VA

Harvest Pumpkin Fall Centerpiece Workshop

 Sat, 01 Nov at 01:00 pm The Homestead Farm at Fruit Hill Orchard LLC USD 82

Yuletide Mystical Market

 Sun, 14 Dec at 11:00 am Raven Conjure

Breaking Breads

 Sat, 15 Nov at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Holiday Market & Big Schloss Release Day!

 Sat, 29 Nov at 02:00 pm 320 N Cameron St, Winchester, VA

A Christmas Carol

 Thu, 06 Nov Winchester Little Theatre

Christmas Maker’s Market

Sat, 06 Dec at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Holiday Wreath Sale

 Sat, 01 Nov at 10:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

Victory Christmas Bazaar

 Sat, 22 Nov at 08:00 am 2870 Middle Road, Winchester, VA

Gallery Explorers: Winter Landscape Holiday Cards

 Sat, 15 Nov at 10:30 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

A Christmas Carol at Winchester Little Theatre

 Sat, 15 Nov at 08:00 pm Winchester Little Theatre

Winter Wonderland Christmas Market

Sat, 22 Nov at 09:00 am Millwood Station Banquet Hall

A Christmas Carol at Winchester Little Theatre

 Sat, 22 Nov at 08:00 pm Winchester Little Theatre

A Christmas Carol at Winchester Little Theatre

 Sun, 16 Nov at 02:00 pm Winchester Little Theatre

Holiday Scavenger Hunt Fun Run

 Thu, 11 Dec at 06:00 pm Runners' Retreat

Gallery Explorers: Winter Landscape Holiday Cards

 Sat, 20 Dec at 10:30 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

John Mann-Montague Avenue United Women in Faith Holiday Bazaar

 Fri, 07 Nov at 09:00 am 102 Montague Ave Free

West Oaks Holiday Craft Show

 Sat, 29 Nov at 09:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Classic French Holiday Dinner

 Fri, 12 Dec at 06:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Family Luminary

 Wed, 03 Dec at 05:00 pm 314 Hope Dr, Winchester, VA 22601-6800, United States

Heir and a Parent: Holiday Cookie Tree

 Sun, 21 Dec at 02:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Holiday Concert: Yesterday Swing Orchestra

 Sun, 14 Dec at 01:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

A Christmas Carol at Winchester Little Theatre

 Thu, 20 Nov at 08:00 pm Winchester Little Theatre

A Day in the Kitchen: Advanced Macaron

 Sat, 20 Dec at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Gourmet Cookies

 Sat, 13 Dec at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Adult Workshop: Holiday Wreaths

 Sat, 06 Dec at 03:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

A Christmas Carol at Winchester Little Theatre

 Sat, 29 Nov at 08:00 pm Winchester Little Theatre

Heir and a Parent: Christmas Cookie House

 Sat, 13 Dec at 01:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

2025 City of Winchester Old Town Holiday Parade with Winchester Corgis

Mon, 01 Dec at 07:00 pm City of Winchester VA - Local Government

A Christmas Carol at Winchester Little Theatre

 Sun, 23 Nov at 02:00 pm Winchester Little Theatre

🟣 Scout Spark: A Sister Scout’s Social

 Sun, 07 Dec at 03:00 pm Valerie Hill Vineyard & Winery

Artisan/Vendor Holiday Pop-Up Market at Easely Created

 Fri, 28 Nov at 09:00 am Easely Created Winchester

Museum Store Sunday

 Sun, 30 Nov at 10:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

Little Noon Music - Shenandoah Conservatory's Trombone Collective

 Fri, 05 Dec at 12:00 pm 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

Teen Art Club: Holiday Crafts

 Thu, 11 Dec at 04:30 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Gallery Explorers: Winter Landscape Holiday Cards

 Tue, 16 Dec at 10:30 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

Pictures with Santa @ West Oaks

 Sat, 13 Dec at 10:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

2025 Shenandoah Potters Guild Annual Holiday Pottery Show & Sale

 Sat, 29 Nov at 10:00 am 1460 University Dr, Winchester, VA 22601, United States

A Christmas Carol at Winchester Little Theatre

 Thu, 13 Nov at 08:00 pm Winchester Little Theatre

SPCA Thrift Black Friday Blowout - November 28th

 Fri, 28 Nov at 07:00 am 1944 Abrams Creek, Winchester, VA, United States, Virginia 22601

Holiday Tea

 Tue, 09 Dec at 02:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Holiday Tea

 Tue, 09 Dec at 10:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

Holiday Bluegrass Concert: Jack Dunlap

 Sun, 07 Dec at 03:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Adult Workshop: Holiday Centerpiece

 Thu, 11 Dec at 06:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Adult Workshop: Woven Ornaments

 Sat, 06 Dec at 10:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

Adult Workshop: Woven Ornaments

 Sat, 06 Dec at 02:30 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Adult Workshop: Holiday Centerpiece

 Thu, 11 Dec at 01:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Homeschool Wednesday Workshop: Holiday Ornaments

 Wed, 03 Dec at 10:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601