Major Events

Old Town Summer Vibe

For the past several years, visitors to Old Town Winchester have grown accustomed to a familiar tradition of summer events. Faced with the continuing ...

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 – CANCELLED

Unwind and enjoy all that Old Town Winchester has to offer at Friday Night Live (FNL). Returning for an eighth year, Friday Night Live is the perfect ...

Family Movies on the Mall

In response to the COVID-19 pandemic and guidelines for large gatherings, the Family Movies on the Mall series has been cancelled for the remainder of...

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, ...