It was formed as part of the initial system in 1918, and always ran from the North Carolina state line through Danville, Lynchburg, and Lexington to West Virginia.

In the 1933 renumbering, the piece from Lynchburg to Lexington, including the Glasgow-Lexington section, became U.S. Route 501, as US 60 was rerouted to the north east of Lexington; all of SR 14 was removed in the 1933 renumbering.

At its peak, it ran from near Powhatan to Sperryville via Columbia, Louisa, Orange, and Madison.

In 1921, the State Highway Commission recommended that the legislature relocate SR 16 to run via Sperryville and Thornton Gap rather than Stanley to "eliminate a very difficult and expensive crossing of the Blue Ridge" and provide "a direct connection with the Lee Highway at Sperryville".

[4] Tolls were removed in 1919 when the turnpike company gave the road to the state.