Festivals in Winchester

Check out happening festivals events all around Winchester, VA

Hop Blossom Craft Beer Festival 2026

 Sat, 06 Jun at 12:00 pm Old Town Winchester USD 9 to 39

Independence at the Park - Red, White, and Boom!

 Fri, 03 Jul at 12:00 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Red, White, & Lights! Drone Show

 Sat, 30 May at 09:00 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Strawberry Festival

Sat, 23 May at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Peach Festival

 Sat, 08 Aug at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

NAACP Winchester Area Juneteenth 2026

 Sun, 14 Jun at 12:00 pm Museum of the Shenandoah Valley

Sunflower Festival

Sat, 12 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

Strawberry Festival

 Sat, 23 May at 05:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602 4305 Middle Rd, Winchester, VA 22602, United States

Apple Harvest Festival

Sat, 03 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Apple Harvest Festival

 Sat, 10 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Samhain Luna Market 2026

 Sat, 31 Oct at 10:00 am 125 S. Loudoun Street, Winchester, VA

VA250 Fireworks Celebration

 Sat, 11 Jul at 08:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Honeycrisp Festival

 Sat, 05 Sep at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Winchester Police Dept. 5th Annual Auto Show

 Sat, 23 May at 09:00 am 100 W Piccadilly St, Winchester, VA 22601-3916, United States

Peaches & Beaches Festival

Sat, 01 Aug at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Homestead Harvest Festival

Sat, 24 Oct at 10:00 am 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

Flutterby Fairy Festival 2026

 Sat, 06 Jun at 10:00 am 740 Merrimans Ln Winchester, VA

Kids Festival

Sat, 27 Jun at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Celebracion of Winchester

Sat, 19 Sep at 12:00 pm Taylor Pavilion Winchester

Dawg Days of Summer: Hot Dog Crawl

 Sat, 22 Aug at 12:00 pm Old Town Winchester USD 34

Patriotic Festival

 Sat, 11 Jul at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Pumpkin Festival

 Sat, 24 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Pickle-chester

 Sat, 29 Aug at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

The Healing Field of Honor

 Thu, 21 May at 03:00 pm John Handley High School

2026 Winchester Greek Festival

Sat, 22 Aug at 11:00 am 1700 Amherst St, Winchester, VA, United States, Virginia 22601

2026 Wings and Wheels - Winchester, VA

 Sat, 03 Oct at 10:00 am Winchester Regional Airport - OKV

Summer Of Love Scavenger Hunt For Charity

 Sat, 20 Jun at 04:00 pm Winchester Brew Works USD 17 to 30

Fall Harvest Festival

Sat, 17 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

1:8 Scale Summer Outdoor Series

 Sat, 13 Jun at 09:00 am 246 Sulky Dr., Winchester, VA, United States, Virginia 22602