The General Assembly of Virginia incorporated the Alexandria and Harper's Ferry Railroad on 20 March 1847. The rail line was initiated to help Alexandria compete with the Port of Baltimore. Farmers in the Shenandoah Valley had traditionally brought their goods to port in Alexandria, but newly completed rail lines made it easier for them to transport goods by rail to the Port of Baltimore. The City of Alexandria hoped that a new rail line, going west to Harper's Ferry, would recapture some of the lost trade. In 1853, the rail line changed its name to Alexandria, Loudoun, and Hampshire Railroad. Construction on the track began in 1855 at the eastern end.

The tracks reached Leesburg in 1860, but the Civil War disrupted train service and expansion, and Purcellville and Round Hill did not see rail service until 1874. Development stalled after 1874, and the railroad changed hands and names several times until it was acquired by Southern Railway on 1 July 1894. New leadership reinvigorated development, and the line reached Snickersville in 1900. The town changed its name to what it felt was a more sophisticated "Bluemont" to attract visitors from Washington, D.C. Bluemont became the terminus of the line, plans to extend to Winchester or Harper's Ferry were abandoned, and the line became known as the Bluemont Branch of the Southern Railway.

The railroad mainly served farmers in Loudoun and Fairfax Counties, allowing them to easily transport goods to Alexandria. There was passenger service on the trains as well, and the line brought city dwellers from Washington to the bucolic spas and resorts of western Loudoun County. In 1911 the Washington and Old Dominion Railroad (W&OD) was created to control the line. The new corporation was also to convert the line from steam to electric locomotives and connect it to the Great Falls and Old Dominion Railway, a suburban line put in place to take visitors to the newly established park at Great Falls. The original steam locomotives were retired and new, electric "interurbans" began service. This change marked a shift in emphasis from transporting farm goods and stock to transporting people.

Ridership on the W&OD declined during the Great Depression and the railway ended all service beyond Purcellville in 1939. Passenger service was suspended in 1941, though it was restored in a limited way during World War II. The W&OD continued to suffer serious financial difficulties in the post-war years, and ended passenger service in 1951. In 1968, W&OD ceased operations and Virginia Electric and Power Company (VEPCO) purchased the right-of-way for its transmission lines. Northern Virginia Regional Park Authority (NVRPA) quickly began working to acquire the use of the railroad right-of-way in order to create a recreational trail. NVRPA reached an agreement with VEPCO in 1977 and began paving the empty rail bed; the paved trail reached Purcellville in 1988. NVRPA continues to maintain the trail as the Washington & Old Dominion Railroad Regional Park.