 A small piece of SR 53, from the west end at SR 20 towards Monticello, was added to the state highway system in 1930 (along with SR 20 north to Charlottesville) as State Route 714; it became State Route 239 in the 1933 renumbering.In 1941, State Route 20 was extended north from Scottsville to Charlottesville via Blenheim and Overton, absorbing SR 239.SR 20 was shifted west to its current alignment in 1947; at the same time, current SR 53 was upgraded from State Route 642, and a short piece of old SR 20 became SR 53.