As early as the 1870s, railroad surveyors from the Cumberland and Ohio Railroad Company had plans for a railroad from Gallatin to Scottsville. However, the financial ruin of some of the stockholders of that company resulted in the rights-of-way being transferred to the Chesapeake and Nashville Railroad Company.
This line was built in the 1880s, and to get a straight path, the railroad had to make a deep cut through solid rock close to what is now downtown Westmoreland, TN. This cut and the line have achieved some notoriety for the still-standing Westmoreland Littlest Tunnel.
At forty-six and a half feet in length, it's reported to be the shortest railroad tunnel in the United States and possibly the world. The story is that when the cut was dug, the farmer that owned the property, George Washington "Wash" Minnick would have no way to move his cows from one side of the land to the other. The railroad is said to have constructed the tunnel to satisfy the farmer's needs. A second tunnel on the route, two miles south of Westmoreland was called The Big Tunnel.
In July of 1906, the line was sold to the Louisville and Nashville Railroad which had an interchange at Gallatin. One historian said that the L&N bought up several of these short lines just to insure the protection of its territory.
During its prime, the line carried oil south from Scottsville, KY, as well as strawberries, timber, livestock and passengers. Westmoreland saw as many as eight trains a day during the line's best years. Many rail passengers came to the area for lodging at the nearby Epperson Springs Hotel. The 170-room hotel was famous for the supposed medicinal value of the various sulphur waters found there. A fire destroyed the hotel in the 1920s, ending the need for passenger service.
A problem with the route was that it had many high trestles and the maintenance cost of the trestles outweighed the revenue. Another fact that was said to have done in the line was that it didn't connect to another railroad at Scottsville, KY. On December 10th, 1976 the line was abandoned and the rails were pulled up shortly after.
In 1977, the Westmoreland Littlest Tunnel was appointed to the National Register of Historic Places.
On August 24th, 2004, Tennessee Governor Phil Bredesen and Senator Jo Ann Graves announced that the state was granting the town of Westmoreland just over $106,000 to assist in the preservation and rehabilitation of the Littlest Tunnel. Representative Mike McDonald also helped in securing the grant to repair erosion damages to the site.