Events
Now Accepting First Friday Applications!
Calling all artists! Do you want the chance to showcase, demonstrate, or sell your work for free on the Pedestrian Mall? Do you want to meet other art...
Calling all artists! Do you want the chance to showcase, demonstrate, or sell your work for free on the Pedestrian Mall? Do you want to meet other art...
Get a little extra sweetness in your life with our 10th annual Chocolate Escape! Join us in Old Town on February 4 from 2-5pm for specials, discounts,...
2023, we’re ready for you! The Main Street program of Old Town Winchester is happy to present the 2023 year-at-a-glance calendar for special eve...
Out with the old and in with the new! As 2022 draws to a close, we’re looking forward to once again celebrating all across Old Town. While thing...
Deck the mall with boughs of holly…and the rest of Old Town, too! It’s once again time for an old holiday favorite as we partner with the ...
Join us for your new favorite holiday tradition! Winter in Old Town Winchester is about to get a bit more magical as we bring back the Holiday Open Ho...
It’s the most wonderful time of the year! The holiday season is upon us, and there’s no better place to do your most important shopping th...
It’s time for our annual community stakeholder meeting! Please join us Tuesday, October 11 at the new Vibrissa Beer taproom to meet Old T...
The Holiday Parade returns to Old Town in 2022! Hosted by Winchester Parks and Recreation, the parade begins at 7 p.m. on Monday, November 28. The par...
Winchester Pride returns to Old Town this weekend! The Annual Winchester Pride Celebration is back for it’s 3rd year after a 2 year delay with 5...