Winchester Christmas Events

The YDC's 2026 Festival of Trees

302 S Loudoun Street, Winchester, VA 21 Nov 2026

Winchester Winter Village

Old Town Winchester 6 Dec 2026

Sip and Paint "Vintage Christmas Tree" Bisque Workshop AT Easely Created

Easely Created Winchester 21 Nov 2026

Yule Luna Market 2026

125 S. Loudoun Street, Winchester, VA 28 Nov 2026

Plaid Friday

Old Town Winchester Walking Mall 27 Nov 2026

FREE!! Mark your calendar for 🎅 Cookies, Cocoa & Santa! 🎄

509 Amherst St., Winchester, VA, United States, Virginia 22601 28 Nov 2026

Faith, Love and Laughter - A Country Christmas

252 Costello Drive Winchester Va. 22602 5 Dec 2026

Winter Village at Moon Phased

125 S. Loudoun Street, Winchester, VA 5 Dec 2026

Donuts with Santa and A Christmas Craft Market

3035 Cedar Creek Grade, Winchester, VA 19 Dec 2026

The Old Town Cookie Crawl

Old Town Winchester 12 Dec 2026

Chick-fil-A Christmas Party

112 Market St, Winchester, VA 22603 3 Dec 2026

Chick-fil-A Christmas Party

Chick-fil-A Pleasant Valley Road (2230 S Pleasant Valley Rd, ) 8 Dec 2026

Holiday Tree Jamboree

Winchester Area SPCA Thrift Shop 6 Dec 2026

Literacy Goes to Pemberley! Benefit Showing at WLT

Winchester Little Theatre 12 Nov 2026

Messiah Sing Along

First Baptist Church Winchester, VA 29 Nov 2026

Heir and a Parent: Holiday Cookie Tree

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 19 Dec 2026

Christmas at the Movies - Guildhall Winchester

Guildhall Winchester 23 Dec 2026

Photos with Santa at SVO!

1705 Amherst St., Suite 103, Winchester, VA 28 Nov 2026

Sounds of the Season

205 W Piccadilly St, Winchester, VA 22601-3906, United States 21 Nov 2026

KIDS NIGHT OUT "Holiday Themed" AGES 6-12 at Easely Created

Easely Created Winchester 11 Dec 2026

Pictures with Santa

1597 Senseny Rd, Winchester, VA 19 Dec 2026

Ugly Sweater Contest & Thieves Christmas!

1730 Berryville Pike, Winchester, VA 5 Dec 2026

🎄Love the Locals Christmas Market🎄

832 Berryville Ave, Winchester, VA 21 Nov 2026

YDC Festival of Trees - STREST, LLC (Approved Vendor)

302 S Loudoun St, Winchester, VA 22601-4638, United States 21 Nov 2026

Elves Workshop!

19 W Cork St, Winchester, VA, United States, Virginia 22601 6 Dec 2026

The Bule Ridge Singers Present: O Radiant Dawn

First Baptist Church, West Piccadilly Street, Winchester, VA, USA 12 Dec 2026

The Reflex: The Ultimate 80's Tribute Band - 18+

Bright Box Theater 19 Dec 2026

First Baptist Lessons & Carols

205 W Piccadilly St, Winchester, VA 29 Nov 2026

Holiday Warehouse Market

22 Clark St, Winchester, VA 22601-4848, United States 28 Nov 2026

Sounds of the Season

116 S Loudoun St, Winchester, VA 22601-4722, United States 22 Nov 2026

Tree of Remembrance Ceremony 2026

645 Berryville Avenue, Winchester VA 22601 5 Dec 2026

Clay Gingerbread House

157 N Loudoun St, Winchester, VA, United States, Virginia 22601 15 Nov 2026

Giant Holiday Ornament

2641 Valley Ave, Winchester, VA, United States, Virginia 22601 22 Nov 2026

Santa is coming to Town!

325 W. Boscawen St, Winchester, VA, United States, Virginia 22601 6 Dec 2026

SAVE THE DATE" Tree Lighting Afterparty! Make and Take Ornaments & Hot Cocoa at Easely Created

Easely Created Winchester 5 Dec 2026

SANTALLICA: An Emo, Pop-Punk, & Metalcore Christmas

Bright Box Theater 18 Dec 2026

NSV CVEB Annual Holiday Event

American Red Cross Blood Donation Center 10 Dec 2026

Christmas Dinner and The FOGG Band

1730 Berryville Pike, Winchester, VA 19 Dec 2026

Classic French Holiday Dinner

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 11 Dec 2026

Guest Appreciation Day

170 Costello Dr, Winchester, VA 4 Dec 2026

Sip and Paint "Vintage Christmas Tree" Bisque Workshop AT Easely Created

Easely Created Winchester 29 Nov 2026

MURDER MYSTERY Sip & Paint Night "The Christmas Gala" at Easely Created

Easely Created Winchester 12 Dec 2026

BEGINNER FRIENDLY Chunky Hand Knit Festive Trees at Easely Created

Easely Created Winchester 29 Nov 2026

Bûche de Noël Class

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 20 Dec 2026

The Wickhams - Christmas at Pemberley at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 14 Nov 2026

Winchester, Frederick, Clarke Republican Women Christmas Lunch

Village Square Restaurant 9 Dec 2026

Winchester Holiday Lights Trolley Tour

1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601 11 Dec 2026