The route was never continuous, with gaps filled by secondary routes. The route was at first known as State Route 16 from 1918 to 1940; the State Route 16 designation was needed in the 1940 renumbering to match other states, and so the road was SR 27 from 1940 to the final decommissioning in 1953. The former SR 27 now carries the following designations: State Route 684, U.S. Route 60 near Powhatan to State Route 45 near Cartersville State Route 690, near Cartersville to State Route 6 in Columbia State Route 659, Columbia to U.S. Route 250 at Ferncliff State Route 208, Ferncliff to U.S. Route 33 in Louisa State Route 669 and State Route 612, Louisa to U.S. Route 15 in Orange State Route 230, US 15 at Madison Mills to U.S. Route 29 near Madison State Route 231, Madison to U.S. Route 211 at Sperryville In the initial 1918 state highway system, State Route 16 ran from State Route 2 (now U.S. Route 15) at Madison Mills to State Route 3 (now U.S. Route 11) at New Market via Madison and Luray, crossing the Blue Ridge Mountains at Fishers Gap. North of Madison, this was the path of the Blue Ridge Turnpike. 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". By 1923, SR 16 was truncated to Sperryville; the piece from Sperryville west to New Market became an extension of State Route 21. Major intersections SR 33 State Route 33 was a primary state highway in the U.S. state of Virginia. It was first formed as part of the initial system in 1918; it was State Route 3 until 1923. SR 33 existed until 1933, when it was deemed redundant to the U.S. Routes that used it - U.S. Route 311 (now U.S. Route 220) from North Carolina to Roanoke, and U.S. Route 11 from Roanoke to West Virginia. The number was immediately reused for another route in southeastern Virginia, and in the late 1930s the current State Route 33, an extension of U.S. Route 33, was formed. From Staunton to Winchester, SR 33 was the Valley Turnpike, taken over by the state in 1918. North of Winchester towards Martinsburg,