The bizarre story of this short-lived line traces its roots to 1894 with the Millersburg, Jeromeville and Greenwich Railroad (later the Ashland and Wooster Railway), a railroad primarily built to haul bricks from a brick plant Jeromeville to Custaloga Junction with the Pittsburg, Ft. Wayne and Chicago Railway (later became part of the Pennsylvania Railroad). The line was extended to Ashland in 1899.

Meanwhile, president of the Wabash Railroad, Joseph Ramsey Jr., began planning a rail line to connect the steel mills and docks at Lorain to the Wheeling & Lake Erie mainline (still in use). His line would become the Lorain & West Virginia Railroad. Sometime during this project however, Ramsey either quit or was fired, and the line was completed without him.

Ramsey decided to build a line "on his own," the Lorain and Ashland Railroad, to compete with the L&WV. The line nearly paralleled the L&WV from Lorain to Wellington. Both Lines made it to Lorain in 1906. Ironically, the Lorain & Ashland was never used after its completion, and fell into disrepair. This also gave the L&WV time to establish itself, putting the Lorain & Ashland in a position from which it could not recover.

In 1913, a consolidation of several lines, including Lorain & Ashland and Ashland & Wooster resulted in the Lorain, Ashland and Southern Railroad. By 1915, the portion from Wellington and Ashland was completed, unused portions repaired, and traffic finally began on the full length of the route. Despite the fact that this line would have made a perfect access for the Erie Railroad and Pennsylvania Railroad from their mainlines to Lorain (it is speculated that this was one of Ramsey's intentions), neither used the line. Ramsey later sold half interest of the line to both.

Despite efforts to stay afloat, severe competition and corporate mismanagement caused the company to go under in 1925, effectively abandoning the line. Rails remained until 1942, when the drive for scrap metal for the War resulted in the line being pulled up.

After many years, virtually no trace of the line exists. Most of the ROW has been destroyed by farms and urban sprawl. However, rails remain in pavement in a few streets in Lorain, some bridge abutments remain, and railbed is still visible in some rural areas. Also, interlocking pads can still be found along the Rail-Trail that was once the NYC Mohawk Division.