Winchester Festivals Events

Old Town Trick or Treat

Old Town Winchester Walking Mall 24 Oct 2026

Samhain Luna Market 2026

125 S. Loudoun Street, Winchester, VA 31 Oct 2026

Homestead Harvest Festival

2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 24 Oct 2026

Pumpkin Festival

3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 24 Oct 2026

The Big Cheese Festival

James Charles Winery & Vineyard 24 Oct 2026

The YDC's 2026 Festival of Trees

302 S Loudoun Street, Winchester, VA 21 Nov 2026

West Oaks Small Business Saturday Holiday Craft Show 2026

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

Katie's Country Music Fest

Backseat Events 14 Nov 2026

Four Color Fright Rest 2026!

80 Weems Ln, Winchester, VA, United States, Virginia 22601 24 Oct 2026

Winter Village at Moon Phased

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

Fall Fest

2870 Middle Rd, Winchester, VA, United States, Virginia 22601 28 Oct 2026

2026 Trunk or Treat & Fall Festival

2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603 21 Oct 2026

Homestead Harvest Festival

2502 N Frederick Pike, Winchester, VA 22603-4162, United States 24 Oct 2026

Winchester Elks Lodge - Mack Berry Band (members & guest)

Elks Club 25 Nov 2026