The Shadow
Highland County, Virginia is celebrating “75 Years of Memories in the Mountains” at the 75th Annual Highland County Fair, September 2–5, 2026—a milestone community event packed with family fun, favorite traditions, and all‑new attractions.
MONTEREY, VA (VR)— The Highland County Fair, Virginia’s longest-running small county fair, is back for year 75! From Wednesday, September 2 through Saturday, September 5, the fairgrounds in Monterey will come alive with the sights, sounds, and flavors of one of the region’s most beloved traditions, starting it all out with a 6pm Parade on Wednesday, September 2nd. In addition, a special one-day free kickoff event that will include a Horse Show, Cruise In, and Jousting will start things off on Saturday, August 29 for those who want an earlier day of fun outside of the four traditional days.
This year’s fair is set to deliver an exciting blend of agricultural showcases, live entertainment, high‑energy competitions, and family fun—all packed into a milestone celebration you won’t want to miss. Highlights include:
· Valley Amusement Rides each day with special Family Night pricing on Wednesday, Sept. 2 & special Sunflower Hours on Thursday, Sept. 3
· Mutton Bustin, Junior Rodeo & Bull Riding (Thursday, Sept 3)
· Demolition Derby (Friday, Sept. 4)
· Rabbit Race & Livestock Costume Contest/Obstacle Course (Friday, Sept 4)
· Truck, Tractor & Diesel Truck Pull (Saturday, Sept. 5)
· Dog Show (Saturday, Sept. 5)
· 4-H & FFA Hog, Goat, Sheep, and Beef Livestock Shows and Sale
· Live Music from High Carbon Steel, Gospel Harmony Boys, Jacob Tolliver, The Conner Family, Pains Run, and David King’s Elvis Tribute
· Face Painting, Clogging, Kiddie Show, Cornhole Tournament, Stilt Walker, Magic & NEW Drone Shows
The Fair also features exhibits in arts, crafts, horticulture, baking, photography, taxidermy, and more, showcasing the talents and traditions of Highland County residents. Non-profit food vendors, games, and community spirit round out the experience. This year will feature special historical displays, a commemorative community quilt auction, and free admission to anyone 75 years of age and older.
The Highland County Fair is a collaborative effort of local civic organizations and volunteers, dedicated to celebrating rural heritage and supporting youth development. Admission and vendors are primarily cash-only, and ATMs will be available on-site.
Mark your calendars and bring the whole family—there’s something for everyone at the 75th Annual Highland County Fair!
The Highland County Fair is directly supported by the Highland County Chamber of Commerce, Blue Grass Ruritans, Mill Gap Ruritans, Stonewall Ruritans, Bolar Ruritans, and the Monterey Lions Club. The Platinum Sponsors of the 75th Annual Fair are Huffman Trailer Sales & Service and Burke & Herbert Bank.
The Highland County Fair Association, Inc. Operates as a 501(c)(3), supporting charitable, educational, and community enrichment efforts in Highland County through agriculture, the arts, and hands-on learning experiences. For more information, please visit www.highlandcountyfairva.com.
