Previously an independent railroad which began operation in 1896, the line technically survives as part of Norfolk Southern.

The line was locally known as the "Crooked and Weedy" and "General Robert E. Lee’s Railroad" during its independent operation.

[3] To the west, Bridgewater, Virginia was the original terminus, but the line was extended to Stokesville, a company town, by 1901.

The line was experiencing a downturn in the 1930s, but was revived when bought by Donald W. Thomas on September 1,1938, who was able to purchase more modern equipment.

[4] By the mid-1940s, the Chesapeake Western operated a total of 53.5 miles in the Shenandoah Valley and interchanges with the C&O, N&W, and Southern Railways.