Winterset District Court serves as the district court of Madison county in the Fifth judicial district of Iowa. IS 80 and US 6 catch a small corner of the Northwest portion of Madison county and US 169 and SR 92 meet just to the West of Winterset.

Madison county was established at the beginning of 1846. The county was the birthplace of the actor John Wayne, fact in Winterset, and its covered bridges were a central part of the book and movie "The Bridges of Madison County". John Wayne's birthplace has been restored to appear as it did in the year of his birth and the city is developing a museum, dedicated to the actor, to be located next to the home. The Madison County Historical society maintains a historical complex in Winterset which includes the Bevington-Kaser Mansion, Winterset train depot, Zion church, Tusha school, an agricultural building, the Martin gas station, the Field mercantile store, a law office, log school, post office, blacksmith shop and stone barn. Most of these structures have been moved to this site from other locations in the city and county. Another interesting spot in town is the North River Stone schoolhouse, built in 1874 and continued to operate until 1945. It is now a museum. North River Stone Schoolhouse, Winterset Art Center, Bevinton-Kaser House and Historical Complex, and Clark Tower.