Named in 1787 for Nathaniel Gordon, Gordonsville began as a small way station for travelers on the main road known as the “Fredericksburg Great Road” connecting to the city of Charlottesville from the west and Richmond to the east. Originally consisting of little more than a tavern, this small village was a popular stopping place for such prominent men as, the Marquis de Lafayette, , James Monroe, and Henry Clay. Because of its prime location, Gordonsville soon became a trade center for the surrounding plantations and countryside. In 1839, Virginia’s General Assembly approved a plan to extend the Virginia Central Railroad to the town, linking it to the state capital. The area continued to prosper, and in 1854 the Orange and Alexandria Railroad completed its own line into the town giving Gordonsville, and by extension the Confederate capital at Richmond, access to agricultural goods from the Shenandoah Valley.
As the front lines of the war began to solidify across northern Virginia, Gordonsville became a town of vast strategic importance. Produce and goods from the Shenandoah Valley flowed out along the rail lines. Confederates also took advantage of the connecting lines to transport troops quickly from the Shenandoah Valley to the northern Virginia front, as when Generalcombined forces with General prior to the (1861). As the war progressed, Gordonsville emerged as a central holding station for Confederate detachments as well as the main army. Most prominent, Confederate generals , , , , , and Wade Hampton all bivouacked in the town at various times throughout the war.
Recognizing its importance, the Union army made several failed attempts to capture Gordonsville and thereby cut off the Confederate military and supply line. The closest encounter occurred in June 1864 when Union major general Philip H. Sheridan led a determined cavalry raid in the direction of Gordonsville. Confederate cavalry commander Wade Hampton intercepted Sheridan in the vicinity ofabout eight miles away and after a chaotic and dogged fight, repulsed Sheridan from the region.
In addition to Gordonsville’s role as a Confederate supply line, it also housed an important medical hospital. In March 1862, the town’s premier inn, the Exchange Hotel, was converted into a battlefield receiving hospital. During its four-year tenure, the medical center treated more than 70,000 Confederate and captured Union soldiers. During Reconstruction (1865–1877), the Freedman’s Bureau used the hotel as a hospital for newly freed African Americans. Today the restored late-Greek Revival–style Exchange Hotel serves as a Civil War museum.