Virginia's Highland County Fair

Mark Your Calendars!

August 27 – 30, 2025

Horse Show: August 23

Mark Your Calendars!

August 27 – 30, 2025

Horse Show: August 23

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The fair is packed with amusements, games, farm animals, exhibits, and live entertainment

including a demolition derby, truck and tractor pull, live music, clogging, and more!

The Highland County Fair is a combined effort of the:

Monterey Lions Club ~ Stonewall Ruritan Club ~ Blue Grass Ruritan Club

Mill Gap Ruritan Club ~ Bolar Ruritan Club ~ Highland County Chamber of Commerce

June 28, 2025<br /> Gates open at 9:00 am!<br /> Admission:<br /> $15 per person (All-Inclusive)</p> <p>10 and younger FREE</p> <p>(Registration fees &</p> <p>Pit Passes extra)</p> <p>Pit Pass: $25 per person</p> <p> Entrances:<br /> Spectators: Access from Myers-Moon Road/Barn entrance only.<br /> Classic Car Show: Enter through school parking lot.<br /> Demolition Derby & Power Wheels Derby: Use Route 220 Fairgrounds entrance.<br /> **If you’re accompanying a derby driver or car show participant and are not hauling their vehicle, you must enter from the Myers-Moon Road/Barn entrance.</p> <p> Concessions by:<br /> Bolar & Stonewall Ruritan Clubs</p> <p>Mill Gap Ruritans

2025 Sponsors

Gutshall's Exxon services and contact number.
JMW Consulting logo with contact info
Big Valley Performance
B&B Land Management
Wild Man's Diesel Performance

The fair is packed with amusements, games, farm animals, exhibits, and live entertainment including a demolition derby, truck and tractor pull, musical performances, clogging, and more!

The Highland County Fair is a combined effort of the:

Monterey Lions Club

Stonewall Ruritan Club

Blue Grass Ruritan Club

Mill Gap Ruritan Club

Bolar Ruritan Club

Highland County

Chamber of Commerce

Exhibits

Quilt and handmade crafts on display at Highland County Fair in Monterey, Virginia

Paintings, photography, quilts, floral arrangements, big game, and more! View the exhibits our community members worked hard to create this year.

Live Entertainment

Man playing a resonator guitar.

From bluegrass bands and clogging shows to Elvis impersonators and magicians, you never know what’s going to hit the stage at the Highland County Fair!

Livestock Shows

Person guiding pig at animal show

Rally behind our area’s youth as they present the livestock they’ve cultivated this year. A lot of hard work and dedication goes into these farm animals!

Demolition Derby

Demolition derby in front of a cheering crowd.

Always exciting! Grab a burger, hot dog, or ribeye steak sandwich, and head to the grandstand to watch these Frankenstein-like cars battle it out to the bitter end.

Horse Show

Child on horseback receiving award from woman.

The Horse Show is one of the fair’s most time-honored events. Enjoy the skill and finesse of horses and their riders as they compete in timed and performance events.

Truck & Tractor Pull

Farmer driving red tractor in an event

Watch the black smoke fly as these powered-up machines drag the sled down the track. Who will you cheer for? Ford, Chevy, or Dodge?

Food Vendors Welcome </p> <p>Calling all Highland County non-profits! You're warmly invited to apply to join us as a food vendor during the fair. In a brief period, your organisation can significantly boost its financial reserves far more efficiently than through weeks of smaller events.<br /> Start the application process by emailing info@highlandcountyfairva.com

Note: We only consider Highland County non-profit organizations when receiving food vendor applications.

Note: We only consider Highland County non-profit

organizations when receiving food vendor applications.