By the time 1959 rolled around, the Highland County Fair had truly become a fixture of community...
1959 Highland County Fair Keeps the Spirit Going
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Mark Your Calendars!
September 2 – 5, 2026
Horse Show: TBA
Mark Your Calendars!
September 2 – 5, 2026
Horse Show: TBA
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
2025 Highland County Fair Sponsors
Platinum Sponsors
Gold Sponsors
Bronze Sponsors
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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, 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
Paintings, photography, quilts, floral arrangements, big game, and more! View the exhibits our community members worked hard to create this year.
Live Entertainment
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
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
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
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
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
Calling all Highland County Non-Profits!
Apply as a food vendor at this year’s Highland County Fair!
In just a few days, your organization can raise more funds than it might through weeks of smaller events—making it a fun and efficient way to support your goals.
Start the application process by emailing: info@highlandcountyfairva.com
Note: We only consider Highland County non-profit organizations when receiving food vendor applications.
Vendor Opportunity
Over 6,000 Visitors from Nearby Areas attend the fair, providing you with valuable opportunities to:
Expand your service area
Showcase your unique and intriguing produce
Make a memorable impression
Make lots of $$ to support your business and help it grow
Various options available from $150-$550/week
If interested please email info@highlandcountyfairva.com
Free non-profit option