Winchester Festivals Events

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 12 Sep 2026

Fiddles & Fifths 2026

Shenandoah Valley Civil War Museum 12 Sep 2026

Celebracion of Winchester

Taylor Pavilion Winchester 19 Sep 2026

Apple Harvest Festival

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

4th Annual Veterans Festival presented by Capon Valley Bank at Backseat Events!

114 Full House Drive , Winchester, VA, United States, Virginia 22603 19 Sep 2026

Apple Harvest Festival

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

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

Winchester Regional Airport - OKV 3 Oct 2026

Trunk or Treat on Loudoun Street

302 S Loudoun Street, Winchester, VA 17 Oct 2026

South African Wine and Food Festival

Patti's Place 19 Sep 2026

Apple Butter Festival🍎

933 Barley Ln, Winchester, VA 10 Oct 2026

NSV Rotary Rubber Duck Race

Clear Brook Park Winchester Va 12 Sep 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

Samhain Luna Market 2026

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

Fall Harvest Festival

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

The YDC's 2026 Festival of Trees

302 S Loudoun Street, Winchester, VA 21 Nov 2026

Oktoberfest Presented by Alesatian Brewing Company

145 N Loudoun St 26 Sep 2026

September Full Moon Night: Corn Moon

125 S. Loudoun Street, Winchester, VA 26 Sep 2026

Trainwreck LIVE at WOFM Fall Festival

West Oaks Farm Market 17 Oct 2026