#StayHappening

Holiday events in Winchester

Check out happening holiday events all around Winchester, VA

32 upcoming events Winchester, United States Updated 6 Nov 2026

All 32 events in Winchester

Pictures with Santa

Sat, 19 Dec at 10:00 am 1597 Senseny Rd, Winchester, VA
PICTURES-WITH-SANTA

Clay Gingerbread House

Sun, 15 Nov at 11:00 am 157 N Loudoun St, Winchester, VA, United States, Virginia 22601
CHRISTMAS

Giant Holiday Ornament

Sun, 22 Nov at 02:00 pm 2641 Valley Ave, Winchester, VA, United States, Virginia 22601