Happening Next

Winchester Festivals Events

Festivals Happening Next in Winchester, VA

Peach Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 8 Aug 2026
FESTIVALS

Sunflower Festival

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

Dawg Days of Summer: Hot Dog Crawl

 Old Town Winchester 22 Aug 2026
FITNESS USD 18 TO 34

Fiddles & Fifths 2026

 Shenandoah Valley Civil War Museum 12 Sep 2026
FESTIVALS

Sunflower Festival

 2502 N Frederick Pike, Winchester, VA 22603-4162, United States 12 Sep 2026
FESTIVALS

Trunk or Treat on Loudoun Street

 302 S Loudoun Street, Winchester, VA 17 Oct 2026
HALLOWEEN

The YDC's 2026 Festival of Trees

 302 S Loudoun Street, Winchester, VA 21 Nov 2026
FESTIVALS

Apple Harvest Festival

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

Peaches & Beaches Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 1 Aug 2026
FESTIVALS

Apple Harvest Festival

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

Honeycrisp Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 5 Sep 2026
FESTIVALS

Pumpkin Festival

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

Celebracion of Winchester

Taylor Pavilion Winchester 19 Sep 2026
KIDS

Samhain Luna Market 2026

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

Pickle-chester

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

Homestead Harvest Festival

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

Prohibition Party w/ Blair Crimmins + the Hookers & The Hot Mamas

 Bright Box Theater 31 Jul 2026
ENTERTAINMENT

2026 Winchester Greek Festival

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

FAMILY DAY 2026

 598 N. Kent St. (park is located at rear of building), Winchester, VA 2 Aug 2026

2026 Wings and Wheels - Winchester, VA

 Winchester Regional Airport - OKV 3 Oct 2026
CAR-SHOWS

Fall Harvest Festival

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

West Oaks Farm Market ( Peaches & Beaches Festival )

West Oaks Farm Market 1 Aug 2026
FESTIVALS

Playground Pop–Up

 1001 E Cork St, Winchester, VA, United States, Virginia 22601 30 Jul 2026
POP-UPS

South African Wine and Food Festival

 Patti's Place 19 Sep 2026
FOOD-DRINKS USD 45 TO 75

NSV Rotary Rubber Duck Race

Clear Brook Park Winchester Va 12 Sep 2026
SPORTS

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

 West Oaks Farm Market 29 Aug 2026
MUSIC

Six Strings & Bourbon

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 16 Aug 2026
MUSIC

Evolving Sounds

 Goodson Chapel Recital Hall 9 Aug 2026
MUSIC

Trainwreck LIVE at WOFM Fall Festival

 West Oaks Farm Market 17 Oct 2026
MUSIC

Homestead Harvest Festival

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

1:8 Scale Summer Outdoor Series

 246 Sulky Dr., Winchester, VA, United States, Virginia 22602 13 Jun 2026
WORKSHOPS