The road played a crucial role in the American Civil War, saw the first of many mergers in 1867, and eventually became an important part of the modern-day Norfolk Southern rail system.

Construction began in 1850 and was completed in April 1854, when it connected with the Virginia Central Railroad in Orange County.

Farmers from Virginia's Piedmont region, and later, the Shenandoah Valley could more cheaply ship their products, produce, and goods to the markets of Washington, D.C., and Richmond, and to ocean-going vessels berthed at the Potomac River port of Alexandria.

The railroad entered Reconstruction in dire shape, with much of its track ripped up and most of its rolling stock destroyed.

[3] The main exceptions are a short segment between Orange and Gordonsville, which is part of the similarly named Washington Subdivision of the Buckingham Branch Railroad;[4] and the easternmost portion that traveled through Old Town Alexandria to its waterfront, which no longer exists aside from the Hoofs Run Bridge and the Wilkes Street Tunnel.

Revival efforts began in 1968 when an old row tenement on the NE corner of Royal and Wilkes was turned into luxury apartments called Tunnel Flats.

[citation needed] As wharf traffic declined and Alexandria became more suburban, daily trains through the tunnel decreased to two a day.

An employee walked in front of the locomotive as it went down Union Street, stopping to let shoppers and diners move cars that were parked on the tracks.

In 2007-2008, the tunnel was refurbished, receiving steel reinforcement ribs, more and brighter lighting, drainage improvement, and extensive pavement repairs.