Major Events

Chocolate Escape

Escape to Old Town Winchester for Valentine’s shopping specials and indulgent chocolate morsels at the 7th Annual Chocolate Escape on Saturday, ...

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,...

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 ...

Holly Jolly Celebration

Enjoy the holidays in Old Town at the Annual Holly Jolly Celebration on December 14th, 10 a.m. – 5 p.m.! Enjoy caroling and holiday activities i...

KidzFest!

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

Oktoberfest – Oct. 11 & 12

The annual Old Town Winchester Oktoberfest presented by Compass West Realty returns on October 11-12. Attendees will have the opportunity to enjoy Ger...

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 ...

Shenandoah Apple Blossom Festival

Winchester’s most well-known event the Apple Blossom Festival, now in its 92nd year, is an annual event organized by the private Shenandoah Apple Blos...

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. ...