Major Events

Shape Up Sundays

Shape Up Sundays are back to offer a health-oriented monthly series at the Taylor Pavilion. Held one Sunday per month, June through September, each ev...

Oktoberfest – Oct. 12 & 13

The sixth annual Oktoberfest presented by Compass West Realty returns on October 12th and 13th! Attendees will have the opportunity to enjoy German in...

Holly Jolly Celebration

The Old Town Winchester Holly Jolly Celebration returns on December 8th, 2018. More details are coming soon, but check out last year’s event for...

Chocolate Escape

Escape to Old Town Winchester for Valentine’s shopping specials and indulgent chocolate morsels at the 5th Annual Chocolate Escape on Saturday, ...

St. Paddy’s Celtic Fest

Pre-game St. Paddy’s Day with our Third Annual Old Town St. Paddy’s Celtic Fest WINCHESTER, Va – Celebrate the community’s Irish and Scottish heritage...

Shenandoah Apple Blossom Festival

The Shenandoah Apple Blossom Festival is returning to Winchester on April 27th to May 6th.   Winchester’s most well-known event the Apple Blossom Fest...

KidzFest!

Bring the kids downtown for a full day of fun and education at Old Town Winchester’s KidzFest on May 19th from 11am to 5pm! Presented by Valley Pediat...

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). Friday Night Live is the perfect opportunity to meet up with fr...

Family Movies on the Mall

Returning for the summer of 2018 is a Winchester favorite: Family Movies on the Mall. Thanks to the support from Partlow Insurance and Erie Insurance,...