The railroad came to Winterset in 1872 and the depot first sat in the east part of town. It was moved to two blocks north of the Courthouse Square in 1909. The depot was an exciting place to be before automobiles and airplanes came into fashion. Store owners would leave from here to go on buying trips to the East, where they saw the latest products to order for sale in their shops. Families would gather here to tearfully send their sons and fathers off to World War I, and to meet them when they returned. For many years, the train was the only means of transportation to Des Moines. In addition to railroad memorabilia inside the depot, a model railroad is set up outside the building and serves as a site for gatherings of railroad enthusiasts several times a year. Moved to this site in 1984, the depot was restored in 1991.