Winchester Holiday Events

Winchester Winter Village

Old Town Winchester Walking Mall 6 Dec 2025

Victory Christmas Bazaar

2870 Middle Road, Winchester, VA 22 Nov 2025

Yuletide Mystical Market

Raven Conjure 14 Dec 2025

Winter Wonderland Christmas Market

Millwood Station Banquet Hall 22 Nov 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

Solenberger’s Hardware LOVE THE LOCALS

832 Berryville Ave, Winchester, VA 22 Nov 2025

Santa Pub Crawl — Downtown Winchester, VA

15 E Boscawen st, Winchester, VA 5 Dec 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

Holiday Bazaar

164 Poorhouse Rd, Winchester, VA 22 Nov 2025

A Christmas Carol

Winchester Little Theatre 6 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 28 Nov 2025

Pink Friday Boutique Crawl

Old Town Winchester Walking Mall 21 Nov 2025

Go Big and Stay Home

Patti's Place 13 Dec 2025

Winchester Holiday Lights Trolley Tour

1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601 12 Dec 2025

November TalkWALK Community Walk Presented by BikeWalk & Friends of Old Town

Taylor Pavilion Winchester 22 Nov 2025

Library Shop Sale @ Handley Library

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

Swing into the Holidays with Winchester Swing Dance

Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601 11 Dec 2025

SVO Holiday Market & Pictures with Santa

1705 Amherst St., Suite 103, Winchester, VA 29 Nov 2025

SPCA Thrift Black Friday Blowout - November 28th

1944 Abrams Creek Dr, Winchester, VA 22601-4485, United States 28 Nov 2025

CONTEMPO Ensembles

Armstrong Concert Hall 4 Dec 2025

West Oaks Holiday Craft Show

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

Tinsel Tea

The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA 6 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

The Nutcracker Ballet

John Handley High School 13 Dec 2025

Windependent Weekend

Old Town Winchester Walking Mall 28 Nov 2025

🟣 Scout Spark: A Sister Scout’s Social

Valerie Hill Vineyard & Winery 7 Dec 2025

Christmas Market @ The Ivy Room

The Ivy Room 29 Nov 2025

Museum Store Sunday

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

Classic French Holiday Dinner

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

Better Life Conversations: Finding your Happy During the Holidays

14 E Piccadilly Street, Suite 105, Winchester, VA, United States, Virginia 22601 20 Nov 2025

Pictures with Santa @ West Oaks

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

Harry Potter Trivia @ DCBC!

160 N Loudoun St, Winchester, VA, United States, Virginia 22601 17 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

Holiday Concert: Yesterday Swing Orchestra

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

BRS Concert - The Very Best Time of Year...

First Baptist Church Winchester, VA 14 Dec 2025

2025 City of Winchester Holiday Parade

Historic Old Town Winchester, Virginia 1 Dec 2025

Christmas Music Bingo

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

Gourmet Cookies

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

Heir and a Parent: Christmas Cookie House

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

Artisan/Vendor Holiday Pop-Up Market at Easely Created

Easely Created Winchester 28 Nov 2025

Holiday Tree Jamboree

1944 Abrams Creek, Winchester, VA, United States, Virginia 22601 7 Dec 2025

Adult Workshop: Holiday Wreaths

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

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 20 Nov 2025

Elf Movie trivia

4305 Middle Road, Winchester, VA, United States, Virginia 22602 14 Jan 2026

Holiday Scavenger Hunt Fun Run

Runners' Retreat 11 Dec 2025

The Red Gobbo Secret Gift Exchange

255 Market Street, Winchester, VA, United States, Virginia 22603 13 Dec 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 23 Nov 2025

A Day in the Kitchen: Advanced Macaron

27 North Loudoun Street, 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

Holiday Party & Helmet Drive

Winchester Brew Works 2 Dec 2025

Gallery Explorers: Winter Landscape Holiday Cards

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

Family Luminary

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

Holiday PJ Parties at WBW!

320 N Cameron St, Winchester, VA 1 Dec 2025

Heir and a Parent: Holiday Cookie Tree

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

Gift Wrapping Extravaganza

ARE's RISE Center 14 Dec 2025

SAME BRP - 2025 B2B Holiday Social

The George Washington A Wyndham Grand Hotel 4 Dec 2025

Winter Solstice Market at Winter Village

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

Phil Kline’s Unsilent Night

1460 University Dr, Winchester, VA, United States, Virginia 22601 13 Dec 2025

2025 City of Winchester Old Town Holiday Parade with Winchester Corgis

City of Winchester VA - Local Government 1 Dec 2025

Gallery Explorers: Winter Landscape Holiday Cards

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

Four Color Fantasies Pre-Christmas Sale!

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

Fierce Love Rescue at Skyline Harley-Davidson | It's a Paw-liday Extravaganza!

Skyline Harley-Davidson 13 Dec 2025

2025 Shenandoah Potters Guild Annual Holiday Pottery Show & Sale

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