the Winchester and Western Railroad today runs from Winchester southwest to Gore, and north to Hagerstown
Source: Virginia Department of Rail and Public Transportation, Virginia State Railroad Map (2012)
The Winchester & Western Railroad is a shortline with 53 miles of track in the Shenandoah Valley The first stretch to be constructed connected Gore to Winchester, hauling timber products (especially railroad ties) 18 miles to the Baltimore & Ohio (B&O) connection at Winchester. The primary customer was a subsidiary of the railroad, the Winchester Lumber Company. Passenger traffic was minimal.
The railroad was extended to Wardensville, West Virginia in 1921. Various narrow gauge (three-foot) lines were built west of Wardensville to collect timber. The cut-over timberlands produced less material to haul by the 1930's, and during the Great Depression the Winchester and Western abandoned the Gore-Wardensville section.
The Winchester and Western Railroad still operates the Sandman Branch from Gore to Winchester. In 1986, the railroad acquired from Conrail an additional 35 miles of track linking Winchester to Hagerstown, by way of Martinsburg West Virginia.1
That 35-mile stretch had once been part of the Cumberland Valley Railroad. The Pennsylvania Railroad had control of the Cumberland Valley Railroad when it built south to Winchester in 1889. That enabled a connection with the Norfolk and Western Railroad, so the Baltimore & Ohio (B&O) Railroad had competition for shipping Virginia/West Virginia coal to northern customers.
The Cumberland Valley Railroad was merged into the Pennsylvania Railroad in 1919. The Pennsylvania Railroad retained a significant financial interest in the Norfolk and Western Railroad until divestiture was required to gain approval of the 1968 merger with the New York Central and creation of the Penn Central.2
The Today Winchester & Western connects to the CSX at Winchester and Martinsburg, West Virginia. The connection with the Norfolk Southern is at Hagerstown.