Created by the West Yellow Pine Lumber Company

John W. West, of Valdosta, Georgia, with his brothers Eugene E. West and Abram Hunter West, owned the West Yellow Pine Company, in addition to various merchandising, lumbering, and turpentine manufacturing enterprises in Georgia, Florida, Tennessee, and Texas. Based at Olympia, in Lowndes County, Georgia, the West Yellow Pine Company consisted of a lumber mill and a store (possibly a company store). These records indicate that they also incorporated a railway, the Madison Southern Railway.

W.J. Kelly and William P. Smith of Jacksonville, and John W. West chartered the Madison Southern Railway Company in 1906. Their purpose was to build a 60-mile line from Madison southward to Deadman's Bay (now Steinhatchee), Florida. According to Elmer Spear, in his Madison County Florida Family History Book (2002), for reasons unknown, the road was not immediately built. Before and after the turn of the century, several roads were projected to Deadman's Bay with the idea of developing a deep-water port at that location. However, none of these efforts proved fruitful because offshore barrier reefs rendered the construction cost of such a port prohibitive.

The Madison Southern Railroad was finally built in 1909 by the West Yellow Pine Lumber Company, and incorporated by John W. West, W.J. Kelly, and C.P. Kelly of Madison, all prominent lumbermen doing business in Madison County. The lumber company used the Madison Southern to haul lumber from its sawmill at Weston, Florida, 43 miles south of Madison, and from its logging camp at Waco, Florida, three miles south of Weston, to the sawmill. It also hauled lumber from two other sawmills, one at Lillian, Florida and one at Alamo, Florida, five and six miles, respectively, south of Madison, and served a turpentine still owned by C.P. Kelly. The 6.7 mile road was built with 40-pound rails, most of which were leased from the Seaboard Air Line Railroad.

The Madison Southern Railway's original equipment included three locomotives, one passenger car, and 33 freight cars. By 1919, the number of locomotives was reduced to one and the number of freight cars to five.

After several good years of hauling forest products, traffic on the Madison Southern gradually declined. During 1921, according to Spear, only 11,219 tons of inbound and outbound freight were handled and total passenger revenue was only $37.15. By coincidence, the railroad's charter expired on May 22, 1922, about the same time the West Yellow Pine Lumber Company's sawmill was shut down and dismantled. The road and equipment reverted back to the lumber company, which used it to scrap their logging camps and tram roads into the woods. On December 18, 1922, the Madison Southern applied to the Interstate Commerce Commission for permission to abandon the line.