The Winchester & Western was initially constructed in the 1910s, to tap local forests to supply railroad ties to the Baltimore & Ohio. The line was eventually extended to Wardensville, WV in the early 1920s.

Freight traffic on the outer reaches of the branch dwindled during the depression, and the line was cut back to Capon Springs in the mid 1930s. Around WWII the line was cut back further to Gore, and the station of Rock Enon Springs lost service at that time. The rest of the line down to Winchester remains in service, with a sand quarry near Gore providing most of the freight.

The abandoned segment travels through remote valleys along the border of Virginia and West Virginia. Topo maps indicate parts of the abandoned railroad grade but they are difficult to locate. Rock Enon is now a Boy Scout camp.