[1] An existing Northern Central Railway branch line terminating at Owings Mills was used to connect into Baltimore.

The WM built a connection from Hagerstown to Williamsport, in order to access coal traffic from the Chesapeake and Ohio Canal.

[5] Under the leadership of company president John Mifflin Hood, the railway made its first extension into Pennsylvania by leasing a line from Edgemont, Maryland, to Waynesboro and Shippensburg.

[1]: 42 The West Virginia Central and Pittsburgh Railway (WVC&P) began as a narrow gauge line in 1880, its name and gauge changed in 1881 and in the ensuing years it opened a huge swath of timber and coal territory in the Allegheny Highlands of West Virginia.

The Fuller Syndicate, led by George Gould, purchased a controlling interest in the WM in 1902 and made plans for westward expansion of the system.

[1]: 42–43 In 1904, the WM completed construction of a large marine terminal at Port Covington, on the Patapsco River in Baltimore, to support the Gould organization's expansion plans.

The terminal facilities included coal, grain and merchandise piers, overhead cranes, eleven rail yards, warehouses, a roundhouse, a turntable and a machine shop.

In 1927, the WM abandoned some of the GC&C track and accessed additional mines in the area through trackage rights on the Cumberland and Pennsylvania Railroad (C&P).

[5]: 68 Although never a giant, the Connellsville subdivision of WM handled through-midwest fast freight traffic and coal from company-owned mines near Fairmont and Somerset, Pennsylvania.

[7] This led to the area by the station (a half mile from town) and factory being called Asbestos, Maryland at least into the 1930s.

This line, famous for its Black Water Grade in Blackwater Canyon, became an important part of the Western Maryland's success until its eventual abandonment in the 1970s.

In 1929, WM's purchase of a line from the West Virginia Midland Railway extended the GC&E sub southward to Webster Springs.

[5] The Fuller Syndicate attempted to assemble its own transcontinental railroad system beginning around 1902, by acquiring various rail lines.

It faced stiff competition from the Pennsylvania Railroad (PRR), the B&O and others, and became financially overextended in its expansion plans.

A new corporation, the Western Maryland Railway Company, was formed and purchased the WM assets in 1909, and the receivership ended in 1910.

[15][16] Passenger service on its final remaining line, a three day a week mixed train between Elkins and Durbin, West Virginia, ended in 1959.

[17][1]: Chp.V In 1964, the C&O and the B&O jointly filed for permission to acquire control of the Western Maryland Railway with the Interstate Commerce Commission (ICC).

Much of the original WM west of Big Pool has been abandoned including the 2,375-foot (724 m) summit of the Allegheny Mountains and the Eastern Continental Divide near Deal, Pennsylvania.