The Virginia General Assembly issued a charter to the O&A on May 28, 1848, to run from Alexandria to Gordonsville. Construction began in 1850 and was completed in April 1854, when it connected with the Virginia Central Railroad in Orange County. Its longtime President was John S. Barbour Jr., Virginia lawyer, part-time delegate and son of U.S. Representative John Strode Barbour. In 1854, the General Assembly granted the O&A the right to build southward from Charlottesville to Lynchburg. O&A paid for trackage rights over Virginia Central tracks from Gordonsville to Charlottesville. In 1860, the southern extension was completed, including lucrative connections to the Virginia and Tennessee Railroad and the South Side Railroad. The O&A also connected with the Manassas Gap Railroad, at Tudor Hall which gave it access to the Shenandoah Valley. The railroad boosted Virginia commerce. 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. Alexandria, Richmond, and Lynchburg also became manufacturing centers. Passengers could travel from Washington to Lynchburg in eight hours instead of enduring a three-day stagecoach journey.
The railroad entered Reconstruction in dire shape, with much of its track ripped up and most of its rolling stock destroyed. However, Barbour rebuilt the railroad with the help of various politically connected financiers and his brother-in-law J.S.B. Thompson. In 1867, the O&A merged with the Manassas Gap Railroad to become the Orange, Alexandria and Manassas Railroad. After the Panic of 1873, the railroad was consolidated into the Virginia Midland Railway, which was controlled by the Baltimore and Ohio Railroad. It later became part of the Richmond and Danville Railroad, which went bankrupt in the Panic of 1893. The following year it was merged into the Southern Railway. A cutoff between Orange and Charlottesville was incorporated in 1876 as the Charlottesville and Rapidan Railroad and opened in 1880. The Southern Railway acquired the line in 1914.
Modern times
In 1982, Southern Railway System joined the Norfolk and Western Railway to form the Norfolk Southern system. The former O&A tracks are also used by Amtrak and Virginia Railway Express operates commuter railroad service along a portion of the historic line. The line from Orange to Gordonsville has been on long-term lease to the C&O Railway, which transferred to CSX, and now CSX subleases to Buckingham Branch Railroad, which operates it as the Orange Subdivision. Among the traces of the original infrastructure are Hoofs Run Bridge and the Wilkes Street Tunnel in Alexandria.