Winchester Festivals Events

Apple Harvest Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 3 Oct 2026

Apple Harvest Festival

3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 10 Oct 2026

Trunk or Treat on Loudoun Street

302 S Loudoun Street, Winchester, VA 17 Oct 2026

2026 Wings and Wheels presented by United Bank - Winchester, VA

Winchester Regional Airport - OKV 3 Oct 2026

Native Plant Festival

1001 E Cork St, Winchester, VA, United States, Virginia 22601 3 Oct 2026

Apple Butter Festival🍎

933 Barley Ln, Winchester, VA 10 Oct 2026

Homestead Harvest Festival

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

Fall Harvest Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 17 Oct 2026

Pumpkin Festival

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

Samhain Luna Market 2026

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

Shenandoah Stampalooza 2026

Holiday Inn Winchester SE-Historic Gateway 2 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

Winter Village at Moon Phased

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

Old Town Trick or Treat

Old Town Winchester Walking Mall 24 Oct 2026

Katie's Country Music Fest

Backseat Events 14 Nov 2026

Trainwreck LIVE at WOFM Fall Festival

West Oaks Farm Market 17 Oct 2026