New This Year!

The Highland County Fair is all about keeping the excitement alive! Every year, we intermingle fresh, new acts with traditional favorites like the Demolition Derby and the Truck and Tractor Pull.  With a new lineup of acts every year, you’re sure to stay entertained. Stay tuned! We’ll be unveiling more new talent soon!

Bullride Mania - Highland County Fair - Monterey, Virginia - bull riding, barrel racing, calf roping

Bullride Mania!

Friday, August 30, 2024
7:00pm at the Grandstand

Get ready for an adrenaline-packed evening of rodeo action! 

Youth Mutton Bustin
(Ages 4-6, under 60 lbs)
Youth Stick Horse Racing
(Ages 12 and younger)

Bull Riding
Barrel Racing
Women’s Breakaway (Calf Roping)

Anyone can enter the bull riding, barrel racing, and breakaway events! Just bring your own riding equipment.

How to Enter: Text your name, the event you’d like to participate in, and mention it’s for the Highland County Fair on 8/30/24 to 717–334–7724.

No registration needed for the youth events until the day of the events. Stick horses are provided but, HELMETS FOR MUTTON BUSTIN ARE NOT PROVIDED. PLEASE BRING YOUR OWN!

Can be a bike helmet, moto helmet, sports helmet, etc. No specialty equipment necessary.

Live bluegrass music - Highland County Fair - Monterey, Virginia

The Crestmen

Thursday, August 29, 2024
4:00 pm under the Big Tent

The Crestmen is a Southern Gospel quartet based out of Staunton, Virginia, located in the heart of the beautiful Shenandoah Valley. For over 40 years, The Crestmen have traveled across the nation spreading the love of Jesus Christ in song with “classic” southern gospel harmony. Faces and names have changed but the message is the same. Jesus Saves.