Major Events

St. Paddy’s Celtic Fest

Celebrate the community’s Irish and Scottish heritage at the annual Old Town St. Paddy’s Celtic Festival on Saturday, March 9th from noon to 9:00 pm. ...

Shenandoah Apple Blossom Festival

The Shenandoah Apple Blossom Festival is returning to Winchester on April 26th to May 5th.   Winchester’s most well-known event the Apple Blossom Fest...

KidzFest!

Old Town Winchester’s popular KidzFest, presented by Valley Pediatric Dentistry, returns Saturday, May 18th. This free, family-friendly event features...

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 ...

Friday Night Live

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

Family Movies on the Mall

Returning for the summer of 2019 is a Winchester favorite: Family Movies on the Mall. Thanks to the support from Partlow Insurance and Erie Insurance,...

Oktoberfest – Oct. 12 & 13

The 7th 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

The Annual Holly Jolly Celebration is returning to Old Town Winchester in 2019 on December 14th! Details are coming soon, but until then see below for...

Chocolate Escape

Escape to Old Town Winchester for Valentine’s shopping specials and indulgent chocolate morsels at the 6th Annual Chocolate Escape on Saturday, ...