Trunk or Treat on Loudoun Street Sat, 17 Oct at 02:30 pm 302 S Loudoun Street, Winchester, VA HALLOWEEN
Apple Harvest Festival Sat, 10 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 FESTIVALS
Pumpkin Festival Sat, 24 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 FESTIVALS
Fall Fun after dark at West Oaks! Fri, 09 Oct 4305 Middle Road, Winchester, VA, United States, Virginia 22602 MUSIC
The YDC's 2026 Festival of Trees Sat, 21 Nov at 10:00 am 302 S Loudoun Street, Winchester, VA FESTIVALS
KIDS NIGHT OUT "SPOOKY HOUSE" AGES 6-12 at Easely Created Fri, 23 Oct at 05:30 pm Easely Created Winchester KIDS
Orchard View Elementary Nest Fest! A Benefit Concert for Frederick County Families in Need Fri, 09 Oct at 05:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602 MUSIC
CD’s 10th Annual Car Show & $5 Propane fill-up Sat, 10 Oct at 09:00 am 2951 Northwestern Pike Winchester Va 23603, Winchester, VA CAR-SHOWS
Shepherd of the Hills Trunk or Treat Sat, 17 Oct at 12:00 pm 200 Sulky Dr (Near Alamo Theater), Winchester, VA, United States, Virginia 22602 NONPROFIT
2026 Trunk or Treat & Fall Festival Wed, 21 Oct at 06:00 pm 2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603 FESTIVALS
Free Fall Festival and Trunk or Treat Sun, 25 Oct at 01:00 pm 181 Nazarene Dr, Winchester, VA, United States, Virginia 22601 FESTIVALS
WILD ADVENTURES: A Smart Zoo Experience in WINCHESTER - Sunday (10/11)!!! Sun, 11 Oct at 12:00 pm Lowe's Home Improvement (2200 S. Pleasant Valley Road, ) KIDS
Oct Guided Tour of Peaceful Fields Sanctuary Sun, 25 Oct at 02:00 pm Peaceful Fields Sanctuary USD 8 FITNESS
FREE! Amherst Commons First Annual Trunk or Treat Sat, 31 Oct at 02:00 pm 509 Amherst St, Winchester, VA 22601-3878, United States TRUNK-OR-TREAT
Sensory Friendly Trunk or Treat Fri, 23 Oct at 04:30 pm 324 Hope Drive, Winchester, VA, United States, Virginia 22601 TRUNK-OR-TREAT
Fall Fest Wed, 28 Oct at 07:00 pm 2870 Middle Rd, Winchester, VA, United States, Virginia 22601 FESTIVALS
🍂🎃 Spend Columbus Day at the Pumpkin Patch! 🎃🍂 Mon, 12 Oct at 10:00 am 933 Barley Ln, Winchester, VA KIDS
Trunk or Treat, at the George Washington Hotel Parking Lot Thu, 29 Oct at 05:45 pm The George Washington Hotel
KIDS NIGHT OUT "Holiday Themed" AGES 6-12 at Easely Created Fri, 11 Dec at 05:30 pm Easely Created Winchester KIDS
Christmas Breakfast with Minnie Sat, 12 Dec at 09:00 am 109 Boundary Avenue, Winchester va BREAKFAST-WITH-SANTA
Bright Box Card Bazaar 2: An Indoor Pokemon Trading Card Vendor Show Sat, 05 Dec at 09:00 am Bright Box Theater BUSINESS
Nov Guided Tour of Peaceful Fields Sanctuary Sun, 22 Nov at 02:00 pm Peaceful Fields Sanctuary USD 8 FITNESS