Fiddles and Fifths Festival

Aug 26, 2022, 12:00 pm to 10:00 pm
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Get ready for an unforgettable weekend in Old Town Winchester as we send off summer with the Fiddles & Fifths Festival–a tribute to the great Appalachian tradition of bluegrass music and the homegrown taste of Virginia bourbon! This FREE street festival event on August 26 + 27 takes place in the heart of Old Town and brings world-class musical performances to our own backyard block party with all your local favorites.

Join us for headliner performances by acclaimed African-American string band EBONY HILLBILLIES and celebrated New Jersey septet RAILROAD EARTH, as well as local opener acts DUNLAP & MABE and LOW RIVER EXPRESS. Explore the great breweries, bars, restaurants, and retailers of Old Town Winchester. Or simply bring your friends and your fiddles downtown to busk in the open air!

Road Closures

The following road closures are being implemented due to this weekend's Fiddles & Fifths Bluegrass & Bourbon Festival in Old Town Winchester.

From 5 pm on August 25 to 8 am on August 28:

  1. Fairfax Lane (Braddock to Cameron)
  2. Loudoun Street (Piccadilly to Baker)

From 8 am on August 26 to 8 am on August 28:

  1. Piccadilly Street (Indian Alley to Cameron)
  2. Eastbound Lane of Piccadilly Street (Braddock to Indian Alley)
  3. Indian Alley (Piccadilly to Fairfax)
  4. Boscawen Street (Indian Alley to Cameron)


Click here for information about parking in Old Town Winchester

Fiddles and Fifths poster