Shopping Events in Winchester

The YDC's 2026 Festival of Trees

Sat, 21 Nov at 10:00 am 302 S Loudoun Street, Winchester, VA

FESTIVALS

Winchester Winter Village

Sun, 06 Dec at 11:00 am Old Town Winchester

HOLIDAY

Plaid Friday

Fri, 27 Nov at 08:00 am Old Town Winchester Walking Mall

West Oaks Small Business Saturday Holiday Craft Show 2026

Sat, 28 Nov at 09:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Yule Luna Market 2026

Sat, 28 Nov at 10:00 am 125 S. Loudoun Street, Winchester, VA

CHRISTMAS

Small Business Saturday

Sat, 28 Nov at 08:00 am Old Town Winchester

Pink Friday Crawl

Fri, 20 Nov at 03:00 pm Old Town Winchester

Winter Village at Moon Phased

Sat, 05 Dec at 12:00 pm 125 S. Loudoun Street, Winchester, VA

HOLIDAY

Community Market at the Local

Fri, 20 Nov at 10:00 am 230 Spring St, Winchester, VA, United States, Virginia 22601

SHOPPING

🎄Love the Locals Christmas Market🎄

Sat, 21 Nov at 09:00 am 832 Berryville Ave, Winchester, VA

ART

Craft Bazaar 2026

Sat, 07 Nov at 10:00 am 1730 Berryville Pike, 22602

HOLIDAY

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

Sat, 21 Nov at 10:00 am 302 S Loudoun St, Winchester, VA 22601-4638, United States

FESTIVALS

Shop Local Sunday

Sun, 29 Nov at 10:00 am Old Town Winchester

Holiday Open House

Fri, 06 Nov at 04:00 pm 202 S Braddock Street, Winchester, VA

Holiday Warehouse Market

Sat, 28 Nov at 08:00 am 22 Clark St, Winchester, VA 22601-4848, United States

Black Friday Event

Fri, 27 Nov at 07:00 am 1944 Abrams Creek, Winchester, VA, United States, Virginia 22601

BLACK-FRIDAY

Bright Box Card Bazaar 2: An Indoor Pokemon Trading Card Vendor Show

Sat, 05 Dec at 09:00 am Bright Box Theater

BUSINESS

Bazaar - Knit2Give

Sat, 14 Nov at 09:00 am 75 Merrimans Ln, Winchester, VA 22601-6203, United States

Jingle & Mingle | Mom's Night Out

Fri, 04 Dec at 06:30 pm Godfrey Miller Center

SHOPPING