Fall Festivals in Winchester

Check out happening fall festivals events all around Winchester, VA

West Oaks Apple Harvest Festival!

Sun, 05 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Farm & Maker’s Saturday Market

Sat, 25 Oct at 10:00 am 2502 N. Frederick Pike, Winchester, VA

2025 Winchester Medical Center NICU Reunion

Sun, 12 Oct at 01:00 pm West Oaks Farm Market

West Oaks Fall Harvest Festival!

Sun, 19 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

October Yoga in the Gardens

Fri, 03 Oct at 09:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

Harvest Pumpkin Fall Centerpiece Workshop

Sat, 01 Nov at 01:00 pm The Homestead Farm at Fruit Hill Orchard LLC USD 82

2025 Trunk or Treat & Fall Festival

Wed, 22 Oct at 06:30 pm 2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603

Fall Fest 2025

Fri, 17 Oct at 05:30 pm 2333 Roosevelt Blvd., Winchester, VA, United States, Virginia 22601

Bring Your Own Pumpkin- Pumpkin Carving!

Wed, 29 Oct at 04:00 pm 320 N Cameron St, Winchester, VA

Trainwreck LIVE at WOFM Fall Festival

Sat, 18 Oct at 04:00 am 4305 Middle Rd, Winchester, VA 22602, United States

Dill Pickers at West Oaks Farm Market October 11, 2025

Sat, 11 Oct at 12:30 pm West Oaks Farm Market

Trainwreck LIVE at WOFM Fall Festival

Sun, 19 Oct at 01:00 pm West Oaks Farm Market