The first piece of SR 5 was added to the state highway system in 1923, a portion of the road running west from
Charles City for toward
Richmond, and was numbered
State Route 41. were added in 1924, were added in 1925, and the remaining , taking the route to the Richmond city limits, were added in 1927. An extension to the east, heading north from Charles City to
State Route 39 (now
U.S. Route 60) at
Providence Forge, was added in 1926. In the 1928 renumbering of state roads, this was designated as
State Route 413, since a new alignment of SR 41, heading east from Charles City toward
Williamsburg for , was added to the state highway system, as was a piece at the other end, heading west from
State Route 510 (now
State Route 31). A further from the west and from the east were added in 1930 and 1931, and, in 1932, the route was completed from Richmond to Williamsburg, with from the west and from the east. The road from
State Route 32 (now
U.S. Route 15) at
Zion Crossroads east to
Oilville was added to the state highway system by 1923 as
State Route 321. Extensions east from Oilville were added for in 1924, in 1925, By 1927, SR 321 became an extension of SR 41 west from Richmond, and that year the former SR 321 was extended , the rest of the way to Richmond. In Richmond, SR 41 initially used Broad Street, a
hairpin turn through
Chimborazo Park, Fulton Street, Williamsburg Road, Hatcher Street, Newton Road, and New Osborne Turnpike.
State Route 39 from
Shadwell west to
Monterey, now
U.S. Route 250, was part of the initial 1918 state highway system (numbered
State Route 9 until 1923). It initially continued west from Monterey on present US 250, but by 1924 it used current
State Route 84 west to
West Virginia. The road west from Monterey towards
West Virginia Route 56 (now
U.S. Route 250) for was added to the state highway system in 1930 and 1932 as
State Route 835; the remaining mileage to the state line was added in 1933. In the 1933 renumbering, State Routes 41 and 835 both became part of a new
State Route 5, as did the piece of
State Route 39 from
Monterey to
Shadwell. By 1935, the whole route west of
Richmond became an extension of
U.S. Route 250 into Virginia, truncating SR 5 to its present Richmond-
Williamsburg route. SR 5 was extended east along
State Route 31 through Williamsburg to
State Route 168 (now
State Route 143) "to improve the service to travelers interchanging between Route 5 and Routes
60 and 168" in 1958. SR 31 has since been truncated to the SR 5 junction. ==Major intersections==