By the time 1959 rolled around, the Highland County Fair had truly become a fixture of community life — and this year proved just how far it had come. With fresh leadership, creative entertainment, and strong community ties, the fairgrounds buzzed with new ideas and...
News & Updates
Big Ideas, Baby Shows, & Bingo: 1958 Fair Makes Its Mark
Planning for the 1958 Highland County Fair started early — as in January 14th early. And good thing it did! That year brought a slew of new ideas, fresh faces, and first-ever events that made it clear: the Fair was growing into something special. New Year, New Energy...
Big Changes & Bigger Fun: New Additions in 1957
The 1957 Highland County Fair brought more than just sunshine and sawdust. With new exhibits, contests, and a flurry of behind-the-scenes upgrades, this year’s event raised the bar. The festivities kicked off on Wednesday, August 28, with the beloved Fair Dance...
Floats, Fun & Fair Skies in 1956: The Highland County Fair Hits Its Stride
The Highland County Fair continued its exciting growth in 1956 by adding an extra day to the festivities — officially becoming a four-day celebration of community, creativity, and country life. Kicking off on Wednesday, August 29 with a lively Fair Dance, the event...
Parades, Pups & “Frosty Boy”: A Look Back at the 1955 Highland County Fair
In the fall of 1955, the hills of Highland County came alive once again with the color, clatter, and community spirit of the annual Highland County Fair. With a unanimous vote from the local civic clubs—Stonewall Ruritans, Monterey Lions, Blue Grass Ruritans, and the...
Knights, Chicks & Carnival Kicks: 1954’s Highland County Fair
In the spring of 1954, something exciting was brewing in Highland County. A group of community leaders — representing the Stonewall and Blue Grass Ruritan Clubs, the Monterey Lions Club, and the Chamber of Commerce — gathered to plan a Fair that would bring the entire...
1953: Tractors, Talent, and a Touch of Trouble
In the fall of 1953, Highland County was gearing up for a bigger, better, and more action-packed county fair. The dates were set—September 10, 11, and 12—and for the first time, the Fair would stretch across three full days. To help kids fully enjoy the fun, the...
Historic Jousting Tournament Crowns Highland’s “Queen of Love and Beauty”
In mid-August 1952, committee members made arrangements to offer a Jousting Tournament as one of the major features of the first official Highland County Fair.
From Pink Elephants to Parading Knights: The Birth of the Highland County Fair
From a Pink Elephant Sale to parading knights for the Jousting Tournament, the first official Highland County Fair paved the way for future events.
Bake Sales and Big Dreams: The 1951 Fundraiser That Helped Shape Highland County
In 1951, Highland County, Virginia, organizations and individuals came together to organize what would become one of our area’s main events for decades to come.