Winchester Festivals Events

Dawg Days of Summer: Hot Dog Crawl

Old Town Winchester 22 Aug 2026

Sunflower Festival

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

Fiddles & Fifths 2026

Shenandoah Valley Civil War Museum 12 Sep 2026

Tyler Booth w/ James Tamelcoff

Bright Box Theater 22 Aug 2026

2026 Winchester Greek Festival

1700 Amherst St, Winchester, VA, United States, Virginia 22601 22 Aug 2026

Pickle-chester

4305 Middle Road, Winchester, VA, United States, Virginia 22602 29 Aug 2026

Honeycrisp Festival

3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 5 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

PICKLECHESTER! Dill Pickers at West Oaks Farm Market Saturday, August 29, 2026

West Oaks Farm Market 29 Aug 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

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

South African Wine and Food Festival

Patti's Place 19 Sep 2026

Samhain Luna Market 2026

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

The YDC's 2026 Festival of Trees

302 S Loudoun Street, Winchester, VA 21 Nov 2026

Pumpkin Festival

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

Fall Harvest Festival

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