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

Yuletide Mystical Market

 Sun, 14 Dec at 11:00 am Raven Conjure

Yule Luna Market 2025

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

Santa Pub Crawl — Downtown Winchester, VA

 Fri, 05 Dec at 05:00 pm 15 E Boscawen st, Winchester, VA

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

Calypso Harp Duo: Songs of Light

 Sun, 07 Dec at 04:00 pm Grace Evangelical Lutheran Church, West Boscawen Street, Winchester, VA, USA Free

A Christmas Carol at Winchester Little Theatre

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

Adult Workshop: Holiday Wreaths

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

Christmas Maker’s Market

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

"Clue Christmas" - A Murder Mystery Comedy Show // 7PM SHOW

 Sat, 13 Dec at 07:00 pm Bright Box Theater

Winchester Holiday Lights Trolley Tour

 Fri, 12 Dec at 08:00 pm 1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601

Go Big and Stay Home

 Sat, 13 Dec at 04:15 pm Patti's Place USD 87

Abram's Delight Candlelight Tour

 Fri, 05 Dec at 06:00 pm 1340 S. Pleasant Valley Road, 22601

West Oaks Holiday Craft Show

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

Swing into the Holidays with Winchester Swing Dance

 Thu, 11 Dec at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Library Shop Sale @ Handley Library

 Sat, 29 Nov at 10:00 am 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

Christmas Market @ The Ivy Room

 Sat, 29 Nov at 10:00 am The Ivy Room

Poinsettia Dish garden Workshop

 Sat, 06 Dec at 02:00 pm 1912 Martinsburg Pike, Winchester, VA

A Day in the Kitchen: Advanced Macaron

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

CONTEMPO Ensembles

 Thu, 04 Dec at 07:30 pm Armstrong Concert Hall

Christmas Tree Lighting

 Sat, 06 Dec at 06:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

🟣 Scout Spark: A Sister Scout’s Social

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

Holiday House Tour in Historic Winchester

 Sun, 07 Dec at 12:00 pm 407 S Washington St, Winchester, VA 22601-4032, United States

Abram's Delight Candlelight Tour

 Sat, 06 Dec at 03:00 pm 1340 S. Pleasant Valley Road, 22601

SVO Holiday Market & Pictures with Santa

 Sat, 29 Nov at 11:00 am 1705 Amherst St., Suite 103, Winchester, VA

A Christmas Carol at Winchester Little Theatre

 Fri, 28 Nov at 08:00 pm Winchester Little Theatre

Windependent Weekend

 Fri, 28 Nov at 10:00 am Old Town Winchester Walking Mall

Pictures with Santa @ West Oaks

 Sat, 13 Dec at 10:00 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

Museum Store Sunday

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

Harry Potter Trivia @ DCBC!

 Wed, 17 Dec at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

Holiday Vendor Market @ Vibrissa Winchester

 Sun, 07 Dec at 01:00 pm Vibrissa Beer (Winchester, VA)

Bake Sale ,get your holiday hugs with Santa and the Grinch!

 Sat, 06 Dec at 12:00 pm 164 Poorhouse Rd, Winchester, VA, United States, Virginia 22602

Candlelight Yoga Soothe 🌟🎄🕯️

 Sun, 21 Dec at 02:00 pm Shine Yoga

Italia Performing Arts Institute GIFT WRAPPING FUNDRAISER

Sun, 07 Dec at 10:00 am Winchester Book Gallery

2025 City of Winchester Holiday Parade

 Mon, 01 Dec at 07:00 pm Historic Old Town Winchester, Virginia

Holiday Tree Jamboree

Sun, 07 Dec at 12:00 pm 1944 Abrams Creek, Winchester, VA, United States, Virginia 22601

2nd Annual Grinchmas Show at the Bright Box Theater

Sun, 21 Dec at 02:00 pm Bright Box Theater

Artisan/Vendor Holiday Pop-Up Market at Easely Created

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

Heir and a Parent: Christmas Cookie House

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

SPCA Thrift Black Friday Blowout - November 28th

 Fri, 28 Nov at 12:00 pm 1944 Abrams Creek Dr, Winchester, VA 22601-4485, United States

Gourmet Cookies

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

Christmas Music Bingo

Wed, 17 Dec at 06:30 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Tinsel Tea

 Sat, 06 Dec at 01:00 pm The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA USD 34 to 55

Legacy Christian Academy Christmas Concert

 Tue, 16 Dec at 06:30 pm Daniel Morgan Middle School Free

The Red Gobbo Secret Gift Exchange

 Sat, 13 Dec at 11:00 am 255 Market Street, Winchester, VA, United States, Virginia 22603

Gallery Explorers: Winter Landscape Holiday Cards

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

Holiday Scavenger Hunt Fun Run

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

The Nutcracker Ballet

 Sat, 13 Dec at 02:00 pm John Handley High School

Winterfest Open House

 Mon, 08 Dec at 06:00 pm 302 S Loudoun Street, Winchester, VA

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

Holiday Party & Helmet Drive

 Tue, 02 Dec at 06:00 pm Winchester Brew Works

Family Luminary

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

Holiday PJ Parties at WBW!

 Mon, 01 Dec at 06:00 pm 320 N Cameron St, Winchester, VA

Holiday Concert: Yesterday Swing Orchestra

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

Elf Movie trivia

 Wed, 14 Jan at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Heir and a Parent: Holiday Cookie Tree

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

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

 Sun, 14 Dec at 03:00 pm First Baptist Church Winchester, VA

SAME BRP - 2025 B2B Holiday Social

 Thu, 04 Dec at 01:30 pm The George Washington A Wyndham Grand Hotel USD 0 to 215

2025 City of Winchester Old Town Holiday Parade with Winchester Corgis

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

Winter Solstice Market at Winter Village

Sat, 06 Dec at 12:00 pm 125 S. Loudoun Street, Winchester, VA

Phil Kline’s Unsilent Night

 Sat, 13 Dec at 05:30 pm 1460 University Dr, Winchester, VA, United States, Virginia 22601

Four Color Fantasies Pre-Christmas Sale!

 Sat, 06 Dec at 12:00 pm 80 Weems Ln, 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

Gift Wrapping Extravaganza

 Sun, 14 Dec at 12:00 pm ARE's RISE Center

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

 Sat, 13 Dec at 10:00 am Skyline Harley-Davidson

2025 Shenandoah Potters Guild Annual Holiday Pottery Show & Sale

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

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