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
With Glen Hammer returning as President and Betty Hansel keeping the books as Treasurer, the Fair was in capable hands. But this year’s planning meetings also brought fresh energy, constructive feedback, and some exciting decisions. For starters, the Fair Association officially joined the Virginia Association of Fairs — a sign that Highland’s hometown event was becoming something much bigger.
They also tackled the to-do list head-on:
- Fair catalogs needed to be out earlier. (May was the new target.)
- Saturday’s programming needed a boost.
- The Baby Show deserved a better setup.
- Judging crowds needed more elbow room.
- And events? They needed to start on time.
These weren’t just notes — they were a sign that folks cared deeply about the Fair and wanted it to thrive.
Fresh Events & Firsts
The 1958 Fair brought in new attractions and creative contests that added spark to the schedule. One of the biggest hits? The first-ever Archery Contest. Bullseyes and bragging rights were on the line as contestants tested their aim.
Also making its debut was a Dress Revue, where FHA girls modeled their handmade clothing — accessories and all. Held on Thursday, August 28, it was both a fashion show and a proud display of skill and style.
And in true Highland Fair fashion, the Highland FFA hosted a Turtle Derby — yes, you read that right — as part of the Fair’s growing list of lighthearted competitions.
Wrestling Matches & Carnival Contracts
What would a Fair be without some good ol’ spectacle? Plans for a wrestling match were tossed around, with promoters from Stanley, Virginia, bringing talent and pricing to the table. Meanwhile, the Glades Amusement Company was booked after an in-person visit to Madison, Virginia — bringing rides, games, and that unmistakable scent of cotton candy in the air.
To keep everything running smoothly, tents were rented from the Norfolk Tent Company (at a $40 savings, no less!), and tables were borrowed from the school cafeteria. Mr. D.O. Bird graciously allowed his land to be used for Fair parking — and in return, he received four season tickets.
Concession Stand Fun
The fairgrounds were dotted with colorful booths, each more tempting than the last. Concession highlights included:
- Stonewall Ruritans with their famous Huckle Buck and Dart Game
- Bullpasture Women’s Club serving up milk and ice cream
- Beulah Church ladies offering donuts and coffee
- V.F.W.’s Penny Pitch
- Monterey Lions Club Milk Bottle Toss
- Highland FFA’s Turtle Derby
- Highland Chamber of Commerce’s helium balloons and Ring Toss
- And let’s not forget the Fire Department’s Pop Gun and Ring Pitch
These homegrown games and treats weren’t just fundraisers — they were tradition in the making.
Art Meets Agriculture
This year also saw the launch of a catalog cover art contest for local students. Each school was given $6 in prize money to award their top three young artists. The winning drawing would be chosen for the Fair’s catalog cover — and in 1958, that honor went to Nancy Hammer of Blue Grass. Her artwork set the tone for a fair that celebrated creativity, community, and homegrown pride.
Whether you came for the dress revue, the donuts, or the dart games, the 1958 Highland County Fair had something for everyone — and marked a turning point in its growth from a local gathering to a regional showcase.
Next up: 1959 — where big things (and maybe a few more turtles) are just around the corner.