Events and Things to Do in Berryville, VA

Sunday, September 27

Featured

Hail to the Trail!

SEP

27

1:00 PM

Chapman DeMary Trail, 355 N Hatcher Ave, Purcellville, VA

Bring your family and friends to the 14th annual Hail to the Trail event at the Chapman DeMary Trail on September 27 from 1 to...

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Friday, October 2

Featured

82nd Waterford Fair

OCT

2

10:00 AM

Waterford Foundation, 40222 Fairfax St, Waterford, VA

October 2-4, 2026   Come experience an autumn celebration of Americana at the Waterford Fair, recognized as one of the Sunshine...

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Saturday, September 26

• Shenandoah Valley Fiber Festival

  10:00 am

  Shenandoah Valley Fiber Festival, 890 W Main St, Berryville

  
  

Sunday, September 27

• Hail to the Trail! 1:00 pm

  Chapman DeMary Trail, 355 N Hatcher Ave, Purcellville

  
  
• Morning Worship at John Enders Firehouse

  11:00 am

  John Enders Firehouse, 9 South Buckmarsh, Berryville

  
  
• K-Pop Demon Hunters Family Friendly Dj show!

  12:30 pm

  Bright Box Theater, 15 N Loudoun St, Winchester

  
  

Friday, October 2

• 82nd Waterford Fair 10:00 am

  Waterford Foundation, 40222 Fairfax St, Waterford

  
  

Sunday, October 4

• LC3' Pints 4 Paws Celebration and Fundraiser for Community Cats 12:00 pm

  Vanish Farmwoods Brewery, 42245 Black Hops Ln, Leesburg