Beginning in 1749, Orange County's successive courthouses stood just west of here. In 1854, the Orange & Alexandria Railroad, built to link Alexandria with central Virginia, reached Orange and a train station was built nearby. The 1804 courthouse was replaced in 1859 by the present Italianate structure a block farther west. The buildings around the train station formed one of the town's early commercial districts. A 1908 fire destroyed the original train station and the buildings on the north side of this block. The station and the Main Street structures east and west of it were rebuilt in the early 1900s.
