The Cumberland County Fair in Greenup, IL, has a commitment to horse racing stretching in an unbroken streak to the fair’s inception in 1888. For anyone who attends now, or envisions horse racing in a fair setting, it is intriguing to think of what it may have been like to attend their first day of racing and how it has evolved over the years. One could imagine it being a fun event for people whose way of life revolved around farming, to have a little fun and socialize, all while cheering on favorite horses.

The day’s card of Quarter Horse, Thoroughbred, mule, and pony races on August 18 was my first visit to a fair that also held racing, and it was another racing experience I was eager to have.

The gates to the fairgrounds hung open during a late morning arrival, with each half of the gate decorated with an ornate horse head design.

Outside the racing office, saddle cloths with “Cumberland Co Fair” embroidered on them were neatly folded and stacked, waiting to be placed across the backs of the day’s runners. Immediately surrounding the racing office, horses stood patiently at the end of lead ropes attached to trailers and support posts for barns, while others were stabled at a barn nearest the gap that led onto the half-mile track.

It was a beautiful sunny day, perfect for racing. The track retained a fair amount of moisture on its surface from the previous day’s rains, but the track crew worked diligently to get the track closer to being rated good or even fast.

Ascending the steps on the perimeter of the grandstand and up a narrow wooden walkway to the announcer’s booth granted my first glimpse of the entire track from a more complete vantage point. Trees along the backside formed a barrier, along with a fence, from a nearby road and also created a beautiful backdrop in their lush greenery.

As may be guessed from a fair that has held racing since 1888, there were a lot of knowledgeable and dedicated horsemen on site. It was great to have a conversation between races about grooms and their importance, and horse care and management in general, with Bill Gross, the presiding judge, and to later veer into talking pedigrees—one of my particular obsessions about racehorses.

Fair racing was on my list of racing experiences to have for its unique aspect, and as the races began, it was evident it was going to provide opportunities to add to my racing knowledge, a welcome bonus.

Races restricted to Illinois-bred horses—5 of the 9 on the card, when the mule and pony races are included—were required by the Illinois Department of Agriculture to have at least three horses with three separate owners be entered and also break from the gate to meet the criteria to receive Illinois Department of Agriculture funding.

The first race of the day was a Quarter Horse race (the only one on the card specifically for that breed) at 220 yards, won by Bid of Shine in a time of 12 2/5 seconds. Line I One captured the following race, the first Thoroughbred race of the day, covering the four-furlong distance in a time of 59 2/5 seconds.

The third race was not restricted to Illinois-breds, and was able to run with only two entrants, Lucky Song Cat and Midnight Louis. It was a maiden race at 5 furlongs, and in the parlance of fair racing, “maiden” does not mean a horse who has never won a race as one is used to its definition being at pari-mutuel tracks. “Maiden” in this context means a horse who has never won on the fair circuit.

Lucky Song Cat, a gray horse, had been a $26,000 yearling purchase and had been victorious at pari-mutuel tracks. She had a lovely way of moving at a trot that was reminiscent of a dressage horse. Her stride at a run was long and reaching and everything about her revealed class and style, and she won the race, a fair maiden no more.

Schwarzkopf captured race 4 for his jockey Mike James, a regular rider at pari-mutuel tracks, and James rode that streak into the next race aboard Pirates On Line, giving him his fourth consecutive win for the day. Pirates On Line is also a winner of multiple races at the Cumberland County Fair, and his affinity for the track was on display as he crossed the wire in an easy-looking effort, with his ears pricked.

Before the card finale, the Cumberland County Derby at a mile-and-an-eighth, the mule and pony races were held. Fred the mule was the victor over his larger opponent, covering the short distance in front of the grandstand to the wire in a time of a little over 15 seconds.

The ponies, like the mules, also started from a standing position on the track with no starting gate, and several of them showed the distinction between pleasure horses and those conditioned to race when they attempted to run through the gap at the top of the stretch to go back to the barn. No discredit to their riders—just one of those things I’ve heard pleasure horses will attempt from time to time!

The community feel of the racing was a wonderful element, as was the aspect of it drawing spectators for the love of the sport instead of also being driven by potential gambling payouts. It was a great time.

The final race of the day was split into two divisions with two runners each, with the ultimate winner being the horse who finished fastest in the two runnings. Division 1 featured Maelstrom and WW Spring Storm. Maelstrom won in a time of 1:59 4/5, setting the mark for Waz You Doing and Schiller in division 2 of the race.

Schiller, the 2017 winner, successfully defended his title in holding off Waz You Doing and covered the distance in a time of 1:59 2/5, giving him the overall victory against Maelstrom and WW Spring Storm as well, and his jockey Mike James a record six wins in one day at the fair.

With the racing over for another year on the closing day of the fair, the work began to convert the track into a setup for the evening’s Demolition Derby.

It had been a wonderful experience seeing fair racing for the first time, and I look forward to seeing more racing in similar venues in the future.

The interval between the Demolition Derby and the racing was filled with more racing talk, further highlighting how invested and sought-after horsemen from this region can be, as one gentleman shared fascinating stories of D. Wayne Lukas and working for him on the California circuit, and several people gathered were wearing Juddmonte hats, signifying professional ties to one of the most renowned farms in Kentucky.

The devotion to racing is certainly evident at every turn at the Cumberland County Fair, and it is incredible to think of it being conducted for well over a hundred years. It’s more low-key than the tracks that garner headlines on a regular basis, naturally, but no less worthwhile to attend for anyone who has racing in their blood. You’ll be among your kind and conversation about horses will flow naturally even with people you never knew before. What better way to spend a day if you love the sport?

Information about funding and conditions to be met for races to be run, as well as background details about horses entered, were provided by race announcer Kurt Becker’s commentary (drawn from his research) during the course of the race day.