Fair held in same place since 1888
Financial supporters of the 2014 Calumet County Fair are listed on a billboard at the north entrance to the fairgrounds.

The motto “The Biggest Little Fair in Wisconsin” got its start back in 1856 with the first steps in the formation of an Agricultural Society, with the first fair being held in Stockbridge, then moving to other cities and villages over the next several years, including Stockbridge, Brothertown, New Holstein and Lodi (now named Gravesville).

In 1888 Harrison Hobart deeded the land known as Hobart Park to the City of Chilton with the stipulation that the property was to be used for a city park, public pleasure grounds, public fairgrounds and public race course. It was not until after 1888 that the fair had a permanent location. In 1891 the association purchased 8.5 acres from General Hobart adjacent to Hobart Park, in 1898 another parcel of 4.5 acres was purchased from Theador Kersten; in 1926 land was purchased from a German shooting club; this gave the fair all the land from the Manitowoc River to Frances Street; in 1955 another 100 feet was added on the south end which was purchased from Joseph Sell. In 1993 the association added another 40 acres from John Bittner, bringing the total land owned by the association to 56 acres.

On June 15, 1878 a constitution was adopted and registered with the state under the name of Calumet County Trotting Park and Fair Association and with this charter the association was eligible for their first state aid of $100. In March 1891, the official name was changed to the Calumet County Agricultural Association. As the laws have changed, it became necessary to re-codify the Articles and By-Laws, the last time in 1998. Its purpose today is the same as in 1891: “The education of agriculture, mechanical, and household arts. To further enhance the needed educational programs for the benefit of the people of Calumet County. To conduct such exhibitions, fairs, and events consistent with the educational interests and needs of people in Calumet County and the members of this Association.”

Highlighting some of the early milestones from history shows that in 1863 was the first horsemanship and trotting classes were listed for premiums; in 1883 there were a total of 428 entries; in 1891 the one-mile race track was built for $1,100 with the single largest item being engineering for a total of $691. It was completed for the fair dates of Sept. 29, 30, and Oct. 1, 2, with 40 horses entered for the races.