Santa Express

Next date: Saturday, December 13, 2025 | 12:00 PM to 07:00 PM

Bring the kids out to visit Santa inside the caboose along Piccdailly Street. 

Enjoy local caroling groups at 1:00 p.m., 3:30 p.m., and 5:30 p.m.

Pack your appetite and grab your Christmas Cookie Passport, at participating Old Town Merchants, for a delightful journey around the world — one cookie at a time!

“Pop-up” Donation Site for Winchester and the Shenandoah Valley. Donate a new unwrapped toy and brighten a child’s Christmas this year.

Sponsored by City of Winchester, Winchester Economic Development Authority, Friends of Old Town, Toys-For-Tots, & Northern Shenandoah Chapter, NRHS. 

When

Location

Caboose on Piccadilly Street, 231 E Piccadilly St, Winchester, VA, 22601, View Map