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Highland County Fair returns Aug. 27-30 with fun for the whole family

It’s Virginia’s longest-running small county fair

(Highland County Fair)

HIGHLAND COUNTY, Va. – Mark your calendars! The Highland County Fair, Virginia’s longest-running small county fair, is set to return later this month.

From Wednesday, Aug. 27, through Saturday, Aug. 30, the fairgrounds in Monterey will offer agricultural showcases, live entertainment, competitions and other events. A Horse Show will kick off the festivities on Saturday, Aug. 23, followed by a Parade on Wednesday, Aug. 27.

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Here’s the schedule:

  • Aug. 27: Special Family Night pricing
  • Aug. 28: Demolition Derby
  • Aug. 29: Rabbit Race and Livestock Costume Contest/Obstacle Course
  • Aug. 29: New Lumberjack Contests
  • Aug. 30: Truck, Tractor and Diesel Truck Pull
  • Aug. 30: Dog Show

Additional features include:

  • 4-H and FFA Livestock Shows and Sale
  • Live music from Jack & Davis Reid, The Crestmen, Cameron Simmons, Cayden Roberson, Wound Tight and Southern Rail Express
  • Activities such as face painting, clogging, kiddie show, cornhole tournament and Sky High Skyler

The fair will also feature exhibits in arts, crafts, horticulture, baking, photography, taxidermy and more.


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