Major Events
St. Paddy’s Celtic Fest
Celebrate the community’s Irish and Scottish heritage at the 5th annual Old Town Winchester St. Paddy’s Celtic Fest on Saturday, March 7 from noon to ...
Shenandoah Apple Blossom Festival
March 17, 2020: In light of the current COVID-19 pandemic and the CDC’s recent recommendation regarding large gatherings, the Shenandoah Apple Blosso...
KidzFest!
Update March 17, 2020: In response to the Coronavirus (COVID-19) situation, the difficult decision has been made to cancel KidzFest this year. Please...
Friday Night Live
Unwind and enjoy all that Old Town Winchester has to offer at Friday Night Live (FNL). Returning for the eighth year, Friday Night Live is the perfect...
Classic Movies at the Taylor Pavilion
We are happy to announce another great summer season of second Saturday Classic Movie Nights screened by Magic Lantern Theater, Winchester’s classic f...
Family Movies on the Mall
Returning for the summer of 2020 is a Winchester favorite: Family Movies on the Mall. Thanks to the support from Partlow Insurance and Grange Insuranc...
Rockin’ Independence Eve
Celebrate our nation’s independence a day early at Rockin’ Independence Eve, a free, family-oriented event that’s fun for all ages. This All-American ...
Oktoberfest – Oct. 9-10
The 8th annual Oktoberfest will bring German music, dancing and much more to Old Town Winchester! This event is expected to be just as big and excitin...
Holly Jolly Celebration
Come spend time in Old Town this holiday season during our Holly Jolly Celebration on December 12th! Enjoy caroling and holiday activities including f...
Chocolate Escape
Escape to Old Town Winchester for Valentine’s shopping specials and indulgent chocolate morsels at the 7th Annual Chocolate Escape on Saturday, ...