The first residence within the city limits of Darlington was a log house owned by Jamison Hamilton in 1836.

The Mineral Point Railroad reached the town in the fall of 1856, and the citizens were very pleased that their dream of expanding their "village" was finally coming true.

[4] The survey of the original streets and blocks of the community took place in June 1850 by Josiah Richardson and H. H. Gray, assisted by an Indian named January.

[6] Alfred T. Ringling established himself in Darlington, Wisconsin at the age of 20, working as a harness maker in his own shop.

He gave little shows for the students in schools and citizens of Darlington and the surrounding towns, with an act that included having four strong farmers lift up a plow, with Alfred lying beneath it.

Joe Parson, the older of the two, worked in a lumber camp in the winter months in the 1870s.

It was said that he bought a bison that he saw grazing in a field one spring when he was returning from the lumber camp.

[8][full citation needed] The Ringlings had their own band, with Al playing the bass drum, John the cornet, and Charles and Otto the trombone and tuba.

Butch Parson ran the concession wagon, selling items such as pink lemonade, peanuts, popcorn, Cracker Jacks, cigars, and paper fans.

Butch managed the stand and paid a monthly sum to the Ringlings, hired his own help.

By November 1908, Otto Ringling wrote to Butch Parson completely ending the relationship between the two families.

In the letter, he said that the Ringlings could no longer store the concession wagon because of lack of space.

[8][full citation needed] According to the United States Census Bureau, the city has a total area of 1.34 square miles (3.47 km2), all of it land.

As a rural county seat, Darlington's economy is dominated by local government and farm service and food manufacturing related to the Wisconsin dairy industry.

Major employers in the city include Lafayette County government, a Sigma Alimentos Mexican cheese and cream plant, and Wisconsin Whey Protein.

[15] Employment in the dairy industry has attracted a growing number of Hispanic and Latino immigrants to Darlington since the year 2000.

The Pecatonica River Trails Park is a city-maintained campground with 24 sites of river-front camping.

Darlington has a public swimming pool that is open every day from June until August.

[20] Darlington is near Yellowstone Lake State Park, where there is swimming, camping, fishing, and boating.

The Cheese Country Recreational Trail, which is over 50 miles long, can be used by ATV riders.

[20][failed verification] During the summer, there are Friday night stock car races, and a county fair.

The Lafayette County Fair is in July and has displays of livestock, a midway, a carnival, and a concert.

Pecatonica Valley Antique Days are held in September, and the Holiday Open Houses are in November.