There does not seem to be an event of that type in the county again until September 17, 1908, when the predecessor of the now Cherokee County Fair, then known as the Pilot-Rock Plowing Match took place.
The Pilot-Rock Plowing Match, patterned after plowing matches started in Wheaton Township in Will County, Illinois in 1878, derived its name from the contest that was held to determine the best at turning the soil in an area in the best time. Points were given for straightness and neatness of furrows, conformation of furrows, back furrow and also the covering of trash. Any farmer could volunteer as host. This event was a roving affair that traveled from farm to farm each year. A 40 acre field was needed to lay out the match site, and the oat land that would be planted to corn the next year was generally used.
At the first Pilot-Rock Plowing match in 1908, a reported 400 people were fed at the dinner and there were 18 entries for the plowing match itself. By 1912, attendance at the one-day plowing match had grown to 4000 people. 1914 was the last year for the "thresher style" noon dinner, complete with fried chicken, boiled ham, baked beans, mashed potatoes, potato salad and pies, all supplied by the women of the county.
The plowing match was always held on a Thursday in September, and there were other events added as the years went on. as well as more and more exhibits. The first added event was a colt show, then a pulling contest, a poultry show and then ball games with rival teams from nearby townships.
In 1918, they began having tractor classes and livestock exhibits at the Plowing Match, and a year later, in 1919, the event expanded to two days, in order to incorporate all the entries and added events.
At the 1921 annual meeting of the Pilot-Rock Plowing Match Association, the event was first referred to as the "Cherokee County Livestock Show and Farm Bureau Picnic," and in 1922, the Pilot-Rock Plowing match received national fame in the "Country Gentlemen" magazine.
The following year, 1923 , "Wallace's Farmer" magazine, Illinois Central Magazine , and "Chicago Daily Drover" covered the event.
In 1924, "Baby contests" were added to the annual event, and 1937 marked an historical footnote, as the last contest for plowing with horses was held. Two years later, in 1939, "free acts," which had previously performed in the afternoon, were switched to night - time entertainment.
At one point in time, there were reportedly as many as 17 tents set up on someone's farm to accommodate all the things to see and do at the plowing match. When World War II came, the plowing match was suspended, as were many "fun" activities around the country.
When it resumed in 1947, it was difficult to renew the enthusiasm of earlier years. A lot of the skill that was used in the old way of plowing was not needed on the bigger and fancier machines. The Pilot-Rock township plowing match had been a testing place for the big companies for many years, and they could now go to other fairs and talk about their machines, but here they had to prove it.
In 1952, the Pilot-Rock Plowing Match Association bought the property that still is used for the Cherokee County Fair today. In 1953, the site was dedicated and the Pilot-Rock Plowing Match merged with the Cherokee County 4-H Fair. By 1956, the first carnival took place on the grounds, and in 1972, the Pilot-Rock Plowing Match officially changed its name to the Cherokee County Fair.