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!

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

Jack & Davis Reid

Wednesday, August 28, 2024
7:30 pm under the Big Tent

The talented sons of Wilson Fairchild and grandsons of The Statler Brothers. These country music enthusiasts have been touring theaters, fairs, and festivals, amassing a devoted following along the way. They’ve shared the stage with artists like Lorrie Morgan, Gene Watson, Wilson Fairchild, Rhonda Vincent, and Blackhawk. Their authentic country sound will have you dancing, while their humor will keep you laughing all night long. Proudly hailing from Virginia, Jack and Davis Reid are the perfect choice if you’re looking for a fun-filled evening of great country music!

www.JackAndDavisReid.com

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

Sky High Skyler

August 28 – 31
Roaming the Grounds Daily

Sky High Skyler is a professional stilt walker, who incorporates juggling, bubbles, noisemakers, music, balloon hand-outs, animated personality, magic bits, dancing, interacting with unique circus props, humor, high-end character costumes, and more!

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

Cowgirl Circus

August 28 – 31
Roaming the Grounds Daily

The most interactive strolling show at the Fair, Lindsay Grant’s Cowgirl Circus is a fun and educational experience! Lindsay travels all over the fairgrounds on her electric “mootercycle,” teaching lassoing and trick roping to Fairgoers of all ages.

www.CowgirlCircus.com

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.

www.TheCrestmen.com

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.

www.BullrideMania.com

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

Cameron Simmons

Saturday, August 31
3-5 pm under the Big Tent

Cameron is a Highland County native-born and raised in Monterey, Virginia. He found a passion for singing in 2014 and taught himself to play guitar in 2017. He’s excited to share his love of country music with Fairgoers on Saturday night! You don’t want to miss this!