Orange began as one of Virginia's courthouse villages on November 24, 1749, when the justices of Orange County voted to hold county court sessions in Timothy Crosthwait's tavern beside Swift Run Gap Road. A courthouse, jail, law offices, smithies, stores, dwellings for county officers, merchants, and service people, and houses of worship formed the village of Orange Courthouse. In 1854 the Orange and Alexandria railroad greatly strengthened Orange's commercial role by running through the center of the public lot between the courthouse and jail, and after the present courthouse was built five years later, governmental functions shifted a block west while Railroad Avenue grew into the commercial center of Orange County. A state charter created the Town of Orange in 1872, and although railroads later gave way to highways as the main arteries of commerce and the town expanded to include shopping centers and suburban housing, downtown remained the emotional heart and political center of the county. Before dawn on Sunday morning, November 8, 1908, Towles Terrill, a 78-year-old Civil War veteran, accidentally started a fire in his room over Gaines saloon on Railroad Avenue, and by 11:00 A.M. the heart of Orange's business district lay in ashes, destroying all the buildings on Railroad Avenue, structures on both sides of East Main Street between the tracks and Byrd Street, and four buildings west of the tracks on the south side of East Main. The disaster led to the rebuilding of Orange's railroad-centered business district, and every building in the area was constructed between 1909 and 1917 in the commercial style of that era, a character local leaders have worked to preserve. After the Confederate defeat at Gettysburg in July 1863, General Robert E. Lee's army retreated to Orange County and established a defensive position on the south bank of the Rapidan, where it regrouped and resupplied during the winter of 1863-64. The Orange and Alexandria railroad station became the primary supply depot for the Army of Northern Virginia, Confederate soldiers brought in large amounts of rock to macadamize the main street and depot area against the deep mud, and the army's Quartermaster Corps and Provost Marshall maintained offices in town as Lee used Orange County to prepare for General Grant's spring 1864 offensive.
