Happening Next

Winchester Holiday Events

Holiday events Happening Next in Winchester, VA

The YDC's 2026 Festival of Trees

 302 S Loudoun Street, Winchester, VA 21 Nov 2026
FESTIVALS

Thanksgiving Day Buffet at The George Washington Hotel

 103 E Piccadilly St, Winchester, VA, United States, Virginia 22601 26 Nov 2026
THANKSGIVING

Winchester Winter Village

Old Town Winchester 6 Dec 2026
HOLIDAY

West Oaks Small Business Saturday Holiday Craft Show 2026

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 28 Nov 2026

Yule Luna Market 2026

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

Small Business Saturday

 Old Town Winchester 28 Nov 2026
SHOPPING

Faith, Love and Laughter - A Country Christmas

 252 Costello Drive Winchester Va. 22602 5 Dec 2026
ENTERTAINMENT

Winter Village at Moon Phased

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

Chick-fil-A Christmas Party

 112 Market St, Winchester, VA 22603 3 Dec 2026
PARTIES

Pink Friday Crawl

 Old Town Winchester 20 Nov 2026

Chick-fil-A Christmas Party

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

Holiday Tree Jamboree

 Winchester Area SPCA Thrift Shop 6 Dec 2026
MUSIC

Heir and a Parent: Holiday Cookie Tree

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

Christmas at the Movies - Guildhall Winchester

 Guildhall Winchester 23 Dec 2026
ENTERTAINMENT

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

 Easely Created Winchester 11 Dec 2026
KIDS

Pictures with Santa

 1597 Senseny Rd, Winchester, VA 19 Dec 2026
PICTURES-WITH-SANTA

Ugly Sweater Contest & Thieves Christmas!

 1730 Berryville Pike, Winchester, VA 5 Dec 2026
CONTESTS

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

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

Community Market at the Local

 230 Spring St, Winchester, VA, United States, Virginia 22601 20 Nov 2026
SHOPPING

Holiday Warehouse Market

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

Clay Gingerbread House

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

Giant Holiday Ornament

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

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

 Bright Box Theater 18 Dec 2026
FITNESS USD 18

NSV CVEB Annual Holiday Event

 American Red Cross Blood Donation Center 10 Dec 2026
HOLIDAY FREE

Classic French Holiday Dinner

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

Guest Appreciation Day

 170 Costello Dr, Winchester, VA 4 Dec 2026

Small Works: Affordable Art For Everyone

 128 N Loudoun St, Winchester, VA, United States, Virginia 22601 4 Dec 2026
ART

Nov Guided Tour of Peaceful Fields Sanctuary

 Peaceful Fields Sanctuary 22 Nov 2026
FITNESS USD 8

New Year’s Race

 246 Sulky Dr., Winchester, VA, United States, Virginia 22602 2 Jan 2027
NEW-YEAR

Christmas Breakfast with Minnie

 109 Boundary Avenue, Winchester va 12 Dec 2026
BREAKFAST-WITH-SANTA

Jingle & Mingle | Mom's Night Out

 Godfrey Miller Center 4 Dec 2026
SHOPPING

Choral Ensembles: Sounds of the Season

 Armstrong Concert Hall 5 Dec 2026
LIVE-MUSIC

Phil Kline's Unsilent Night

 Old Town Winchester Walking Mall 12 Dec 2026
HOLIDAY

Winchester Holiday Lights Trolley Tour

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