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...
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...
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...
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...
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...
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...