2022 Major Events

WINCHESTER, Va – Old Town Winchester has released its official 2022 major events calendar. The schedule includes seven major events and two ongoing programs between February and December and marks the first full year of event programming since COVID-19 public health concerns caused widespread cancellations and a focus on smaller events. The full list of events can be found online at enjoyotw.com.


Development Services Director Shawn Hershberger is confident this will be a successful and safe step out of the limited offerings of the past two years. “Providing a safe experience while allowing the community to come back together to share in quality arts and entertainment has been the internal focus while making these plans,” stated Mr. Hershberger.


The planned events are structured to highlight the quality of the Old Town business district and provide residents and visitors an opportunity to experience not just excellent entertainment and atmosphere but all of what makes Old Town Winchester such a vibrant community asset. The incredible businesses, unique character, and a wealth of local talent ranging from featured musicians to exceptional culinary arts will be on full display in 2022. The varied slate of events and activities will showcase the culture, character, and excitement that has made Winchester a popular destination.


“Many of the events we are bringing back this year are old favorites. However, some new additions, developed while adapting to disruptions associated with the COVID-19 pandemic, are also included,” added Main Street Program Manager Alex Flanigan.

Currently, the events calendar includes Chocolate Escape on February 5, Celtic Fest on March 12, Rockin’ Independence Eve on July 3, KidzFest on July 9, Fiddles & Fifths Festival on August 26-27, Windependent Weekend from November 25-27, and the Holiday Open House on December 10. In addition, this year will mark the return of Old Town Vibe, the ongoing weekend program which brings live local performers down to the Loudoun Street Mall, and recurring usage of the Old Town Spirit open container license. Other events are in the works as well and will be announced as details become available.


This year’s events season is made possible through the support of the Winchester Economic Development Authority.

EDIT: Updated 6/14/22 to reflect rescheduled events and updated offerings.

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