Originally constructed in the 1850s, the bridge was integral to the Southside Railroad between Petersburg and Lynchburg. As the site of the Battle of High Bridge in April 1865, the bridge played a pivotal role in Lee's retreat in the final days of the American Civil War – and ultimately the war's outcome. Rebuilt after the Civil War to its former dimensions, the 21-span structure was long at a maximum height of above the Appomattox River Valley. The bridge was completely rebuilt in 1914, leaving many of the original masonry piers adjacent to the new structure.