Leeper is named after William T. Leeper, who served as a Captain in the Union Army during the Civil War. In 1871, Leeper convinced the Iron Mountain Railroad to run through his property, although the route would require a cut through two mountains. By 1872, Clarkson Sawmill had moved to Leeper and set up a shop. This immediately caused the rise of Leeper as a "boom-town." Leeper was not actually a town until 1874, by William T. Leeper's son Sid. By 1881, Leeper was a "bona fide" town with a rail station and a post office, and was commonly called Leeper Station. Leeper had then one hotel and four stores. Leeper's hotel, the Ozark Hotel, was considered one of the most elaborate resorts in Southeast Missouri during the early 20th century.