Help us bring Halloween to life by participating in our Spooky Fun: Trolley Trail! We're looking for local businesses, community organizations, schools, clubs, and other groups to decorate a pavilion along the trolley route and create a fun, festive, or spooky display for thousands of visitors to enjoy.
Participation is FREE!
Think you have the best display? The winning pavilion will receive a prize, with the winner determined by votes from the public as they ride the trolley through the trail.
Gather your team, get creative, and join us for one of Winchester's favorite Halloween traditions!
Applications are available now! We can't wait to see what you create! Apply by Wednesday, September 16 at noon.
CLICK TO APPLY
Location: Jim Barnett Park Date: Friday, October 16 Time: 5:30 - 8:00 p.m. Ages: ALL Fee: FREE; Boo Bundles which include Trolley ride tickets are additional fee.
Jim Barnett Park, 1001 E. Cork Street, 22601, View Map
1001 E. Cork Street , 22601
Free
Wednesday, September 16 12:00 p.m.
Friday, October 16, 2026 5:30 - 8:00 p.m.