the Cumberland Valley Railroad linked Hagerstown to Winchester in 1889, and is now part of the Winchester and Western Railroad (built later in 1916)
Source: ESRI, ArcGIS Online
The Cumberland Valley Railroad built south to Winchester in 1889, using a charter issued for the Martinsburg & Potomac Railroad. The Virginia General Assembly approved the merger of the Martinsburg & Potomac Railroad into the Cumberland Valley & Martinsburg Railroad after track was completed.
In fact, the Pennsylvania Railroad controlled the various corporations that built that track to Winchester and operated the trains. Finally, in 1919, the Cumberland Valley Railroad was merged into the Pennsylvania Railroad itself.1
Building south into the Shenandoah Valley was a part of the Pennsylvania Railroad's competition with the Baltimore & Ohio (B&O) Railroad, which had built the Winchester and Potomac Railroad from Harpers Ferry to Winchester in 1836. The 1889 "Martinsburg & Potomac Railroad" extension to Winchester came after other Pennsylvania Railroad efforts to control freight and passenger traffic had not succeded.
After the Civil War, the Virginia General Assembly chartered the Valley Railroad. It was built on the west side of Massanutten Mountain south from Harrisonburg. The Baltimore and Ohio (B&O) Railroad purchased enough stock to ensure control, and its investment financed construction.
At the same time, the Winchester and Strasburg Railroad built track that finally closed the gap between Winchester and Strasburg, and the B&O leased it. The B&O also leased the other railroad which had the right to operate between Strasburg-Harrisonburg.
The B&O was financially stretched, but it ended up with control of track on the western side of the Shenandoah Valley stretching between Harpers Ferry and the southern end of the Valley Railroad. As soon as the Valley Railroad finished construction to meet the Virginia and Tennessee Railroad near Salem, the B&O would be able to pull traffic from the south to Baltimore by way of Winchester to the main liine running through Harpers Ferry.
However, the Valley Railroad was never completed south of Lexington.
The Pennsylvania Railroad sponsored a competing line through the Shenandoah Valley, the Shenandoah Valley Railroad. The Shenandoah Valley Railroad was built east to Winchester, but the Pennsylvania Railroad also pursued building a separate line south of Hagerstown through Winchester towards Staunton.
The Cumberland Valley Railroad laid track from Hagerstown to the Potomac River in 1873, the same year that the Martinsburg and Potomac Railroad built a line further south from that spot on the Potomac River to Martinsburg. When the Martinsburg and Potomac Railroad was sold in foreclosure in 1888, the Cumberland Valley Railroad bought it.
Like the Baltimore and Ohio Railroad, the Pennsylvania Railroad worked through a variety of separately-chartered corporations. By purchasing sufficient amount of stock, the main railroads could appoint directors for the technically-independent corporations which had obtained charters from the legislatures of different states. As the was politically expedient to keep some local business leaders on the boards of the separate corporations, as the Pennsylvania Railroad and Baltimore and Ohio Railroad expanded their systems.
The Shenandoah Valley Railroad started at the Pennsylvania Railroad's line in Hagerstown, Maryland. It too planned a southern junction with the old Virginia and Tennessee Railroad, also near Salem because topography favored that area. In 1882 the Shenandoah Valley Railroad, with funding from northern investors, completed construction to its junction; it grew quickly into the city of Roanoke.
The Pennsylvania Railroad lacked the capital to fund all of its expansion projects. Other investors acquired control of the old Virginia and Tennessee Railroad and the Shenandoah Valley Railroad, and then merged the two into the Norfolk and Western Railroad. That change left the Pennsylvania Railroad as a minority owner. It received substantial dividends, but was unable to control traffic and ensure business increased at Philadelphia rather than Baltimore.
When the Pennsylvania Railroad extended the Cumberland Valley Railroad to Winchester, it did not gain the opportunity to intercept coal traffic already coming from the Appalachian Plateau fields through the Shenandoah Valley. The Shenandoah Valley Railroad (by 1889 part of the Norfolk and Western Railroad) had bypassed Winchester when it built north of Front Royal to Hagerstown.
The Pennsylvania Railroad sought multiple ways to expand its network into the southern states, but the extension of the Cumberland Valley Railroad into the Shenandoah Valley ended at Winchester. Instead, the Pennsylvania relied upon its substantial investment in the Norfolk and Western to generate profits from that part of Virginia.
The Pennsylvania Railroad already had an interchange with the Norfolk and Western Railroad when it financed expansion to Winchester. The Pennsylvania Railroad retained its 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 Penn Central lasted only two years before going bankrupt. In 1976, it was reorganized as Conrail.
Conrail planned to abandon the Hagerstown-Winchester track until the Winchester & Western Railroad acquired the 35 miles. The Winchester and Western's major customer, the sand quarry in Gore, wanted to maintain the link to the Norfolk and Western railroad at Hagerstown. The alternative was to rely upon the Baltimore and Ohio Railroad (by that time part of the Chessie System) and ship via Harper's Ferry, without any opportunity to negotiate competitive rates.
The Winchester and Western Railroad continues to operate on the old Cumberland Valley Railroad, but the terminal in Winchester has been sold.3