In 1858, the first Fair was held at the Courthouse Square in West Bend. Farmers came to the Fair in ox carts. The wooden framed Courthouse housed the exhibits which needed protection from the elements.
Some of the events held included: a plowing match where farmers plowed ¼ acre of stubble ground with horses. The best and shortest time received first premium, trotting matches were also a popular event. $192.75 was paid out in premiums (little over 1% of the premiums paid out today); expenses totaled $19.19 compared to over $600,000 today.