Major Events

Oktoberfest – Oct. 13 & 14

A taste of Germany is returning to Old Town Winchester October 13 & 14 with the 5th annual Oktoberfest. Attendees will sample Bavarian-inspired fo...

Holly Jolly Celebration

The Holly Jolly Celebration will return to Old Town Winchester for 2017 on December 9th! More details are coming soon, but check out last year’s...

Chocolate Escape

Escape to Old Town Winchester for Valentine’s shopping specials and indulgent chocolate morsels at the 4th Annual Chocolate Escape on Saturday, ...

St. Paddy’s Celtic Fest

Old Town Winchester celebrates the community’s Irish and Scottish heritage with the 2nd annual St. Paddy’s Celtic Festival in Old Town Winchester on S...

Shenandoah Apple Blossom Festival

The Shenandoah Apple Blossom Festival is returning to Winchester on April 28th to May 7th.   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 20th.This free, family-friendly event, to be he...

Friday Night Live

Unwind and enjoy all that Old Town Winchester has to offer at the 5th annual Friday Night Live. This great community event is the perfect opportunity ...

Rockin’ Independence Eve

Celebrate America’s birthday early at the fifth annual Rockin’ Independence Eve, presented by Partlow Insurance, in Old Town Winchester on Monday, Jul...

Family Movies on the Mall

Returning for the summer of 2017 is a Winchester favorite: Family Movies on the Mall. Thanks to support from Partlow Insurance and Erie Insurance, thi...

Shape Up Sundays

NEW EVENT: In partnership with Valley Health and its Wellness Center, Old Town Winchester will feature a new event this summer:  Shape Up Sundays. Hel...