Winchester Halloween Events

Old Town Trick or Treat

Old Town Winchester Walking Mall 24 Oct 2026

Samhain Luna Market 2026

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

SPOOKY RIDDIM HOURS - HALLOW'S EVE EDITION

Bright Box Theater 30 Oct 2026

FREE! Amherst Commons First Annual Trunk or Treat

509 Amherst St, Winchester, VA 22601-3878, United States 31 Oct 2026

Spooktacular Scavenger Hunt For Charity

Winchester Brew Works 24 Oct 2026

KIDS NIGHT OUT "SPOOKY HOUSE" AGES 6-12 at Easely Created

Easely Created Winchester 23 Oct 2026

The Old Town Monster Mash

Sweet Caroline's 31 Oct 2026

THE HAUNT | Halloween Bass Takeover @ Blue Fox

1160 Millwood pike Winchester va 24 Oct 2026

The Hawkins Kids Live!

4305 Middle Road, Winchester, VA, United States, Virginia 22602 24 Oct 2026

A Diva's Halloween Special Benefiting Winchester's First LGBTQ Center

Bright Box Theater 24 Oct 2026

Halloween 2026 / Davisson Brothers Band

Backseat Events 31 Oct 2026

Four Color Fright Rest 2026!

80 Weems Ln, Winchester, VA, United States, Virginia 22601 24 Oct 2026

Fall Fest

2870 Middle Rd, Winchester, VA, United States, Virginia 22601 28 Oct 2026

2026 Trunk or Treat & Fall Festival

2581 Northwestern Pike, Winchester, VA, United States, Virginia 22603 21 Oct 2026

Trunk or Treat, at the George Washington Hotel Parking Lot

The George Washington Hotel 29 Oct 2026

Scary Stories After Hours

The YDC 22 Oct 2026

HalloWinchester

Broken Window Brewing Company 24 Oct 2026

Winchester Walking Mall Halloween

Taylor Pavillion Winchester Va 24 Oct 2026

Sensory Friendly Trunk or Treat

324 Hope Drive, Winchester, VA, United States, Virginia 22601 23 Oct 2026

Free Fall Festival and Trunk or Treat

181 Nazarene Dr, Winchester, VA, United States, Virginia 22601 25 Oct 2026

Horror Film Trivia @ Dividing Creek

160 N Loudoun St, Winchester, VA, United States, Virginia 22601 28 Oct 2026

Haunted History Ghost Tours

South end of Loudoun Street Pedestrian Mall, Winchester, Virginia 28 Oct 2026

Spooky Season: Winchester Old Town Ghost Hunt

Old Town Winchester 1 Oct 2026

Halloween at The Wine Room

The Wine Room at Taylor Pavilion 31 Oct 2026

Trunk or Treat 🍭 🚗

2700 Valley Avenue, Winchester, VA 30 Oct 2026

Trunk or Treat By Ambrogi Acres

Backseat Events 30 Oct 2026