A group of investors first tried a railroad in 1837, building it just south of Illinoistown, running southeast to the coal mine. The rail line was built entirely of wood and the investors opened a saw mill in Illinoistown to furnish the lumber. The cost of a wooden railroad proved too expensive and the venture foundered until St. Louis and the state of Illinois provided funds to finish construction. The work was completed near the end of 1837 and the first horse-drawn rail car began to carry coal.
Less than a year later the venture collapsed. St. Louis businessman William G. Anderson acquired the assets in 1838 and made plans for a small steam locomotive to pull the cars. Anderson also extended the line to run north of Illinoistown. Anderson was unable to make the line profitable and it soon lay abandoned. In 1859 the assets were again purchased under the name of the Pittsburgh Railroad and Coal Company, named after Pittsburgh Lake, near the coal mine. Further extending the line past the coal mine to Caseyville allowed the addition of passenger service. Under the new organization the line made stops in Caseyville, Illinoistown, and Brooklyn, north of Illinoistown. This time the line proved successful. In 1869, the owners changed the name to the Illinois and St. Louis Railroad and Coal Company.