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...

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, ...