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!

High Carbon Steel – Classic County Music Show

Wednesday, September 2nd
7:30-10:30 PM  after the Parade under the Big Tent

High Carbon Steel is a rising country band with roots planted deep in the classics. Core members Cory, Dawson, and Nathan form a powerhouse trio whose tight harmonies shape the band’s signature sound. In just a few short years, they’ve built a fanbase in the thousands—and it’s only growing.
The three grew up together on the country music of the 80s and 90s, and eventually found themselves asking the same question many fans have wondered: “Who’s gonna fill their shoes?” That question sparked the creation of High Carbon Steel in 2022.

Since then, the band has worked to honor the emotion and authenticity of the music they love while creating songs that can ignite that same feeling in a new generation. With this mission at their core, High Carbon Steel has taken the stage in cities and venues across Tennessee and beyond. Their steady stream of cover videos on YouTube has helped them build a strong online following as well. They’ve covered a lot of ground since their start—but they’re just getting warmed up. After all, they’ve got some big shoes to fill.

Follow High Carbon Steel Music at https://www.facebook.com/profile.php?id=100090715533235
Check out all their music on their site https://highcarbonsteelmusic.com/home

Orion Skys Drone Show

Taking place each night, on the West Side of the Grounds at the following times:

Wednesday, September 2nd: 9:00-9:15pm
Thursday, September  3rd: 9:00-9:15pm
 Friday, September 4th: 9:30-9:45pm
Saturday, September 5th: 10:00-10:15pm

The Gospel Harmony Boys

Thursday, Sept. 3rd 2026 at 3pm & 5pm under the big tent

The Gospel Harmony Boys are one of America’s longest‑running Southern Gospel quartets, sharing their signature harmonies since 1952. Known for their polished sound, heartfelt ministry, and decades of touring across the country, they’ve performed on major stages, recorded numerous albums, and inspired generations with their commitment to spreading the Gospel through music. Today, they continue that legacy with a blend of classic quartet tradition and fresh, uplifting energy that audiences of all ages love.

Check out all their information at www.gospelharmonyboys.org

Begoon Brothers Bucking Bulls LLC Presents
Mutton Bustin, Jr Rodeo, Barrel Racing, & Rodeo

Thursday, September 3rd, 7:00PM at the Grandstand

4B, LLC is a family owned youth focused miniature bull riding business.

Owned and operated by Wes, Saidee, Ruebin, and Garrett Begoon.

If you have questions or would like to participate please contact 540-569-0606, saideeruth@yahoo.com, or
wesbegoon@gmail.com

New Bluegrass Music for 2026:

Caleb Bailey & Paines Run
The Conner Family

Saturday, September 5, 2026 at 11:00am under the Big Tent

Caleb Bailey & Paine’s Run formed in 2021 after the success of Bailey’s debut album Poplar & Pine. Based in Virginia’s Shenandoah Valley, the band has quickly earned a reputation for high‑energy, heartfelt performances at fairs, festivals, and concert stages across the region. Their newest release on Turnberry Records marks an exciting next chapter and further highlights Bailey as one of bluegrass’s standout young voices.

Bailey comes from deep musical roots, with family ties to recording artists, bluegrass promoters, and touring musicians. Bluegrass Unlimited praises him as “an authentic vocalist” with mature, heartfelt songwriting. His work continues to gain recognition, including a spot in the 2023 IBMA Songwriter Showcase and cuts by artists such as East Nash Grass. His own #1 single, “Grim Reaper,” remains a fan favorite.

With growing national attention and a passion for both tradition and innovation, Caleb Bailey & Paine’s Run are carving out a strong and promising place in today’s bluegrass landscape.
Check out all their information at https://calebbaileymusic.com/home

The Conner Family is a Virginia‑based bluegrass gospel group rooted in family harmony and heartfelt faith. Featuring Vance, Marva, Lisa, and Victor Conner, they share the kind of front‑porch sound that feels right at home in the mountains — warm, sincere, and full of the joy that comes from singing together. Their music blends traditional bluegrass picking with gospel truth, creating a sound that lifts spirits and brings folks together wherever they play.

Check out their Facebook page at https://www.facebook.com/p/Conner-Family-Music-100064841732298/

Jacob Tolliver, Multi-Genre Rock & Roll Pianist

Saturday, September 5, 2026 at 1:30 to 3:30pm under the Big Tent

Jacob Tolliver is an American singer, songwriter, and pianist known for his energetic performances and genre‑blending musical style. As the document notes, he is “known for his energetic performances and genre‑blending musical style” and hails from Portsmouth, Ohio, where his early mastery of piano and love for classic rock ’n’ roll shaped his artistic identity.

He first gained widespread recognition in the Las Vegas production of Million Dollar Quartet, where his “high‑octane piano skills and dynamic stage presence made him a standout.” His success in the role led to the rare opportunity to open on the road for Jerry Lee Lewis, further honing his craft and deepening his connection to the roots of rock ’n’ roll.

Now moving in an exciting new direction, Tolliver is focusing on original music that blends the raw energy of rock with contemporary influences. His evolving sound is described as “both nostalgic and forward‑thinking,” incorporating elements of pop, country, and blues while pushing the boundaries of traditional rock.
As he continues to grow as an artist, Tolliver is poised to make a significant impact with his fresh take on classic sounds, carving out a unique place in the modern music scene.

Check out all his information at https://www.jacobtolliver.com/

Elvis Tribute Artist – David King

Saturday, September 5, 2026 under the Big Tent

2 sets:
4pm Elvis music from the 1950’s-1960’s
5:15pm Elvis during the concert years

Dragon Motorsports Presents the Highland County Fair Truck & Tractor Pull

September 5, 2026 at 5pm at the Grandstand 

Registration begins around 2pm and will end around 4:30pm

Full class rules at https://www.dragonpull.com/

More Information on entry rules and classes can be found here.