Between Charles City County and James City County, it crosses the Chickahominy River via the Judith Stewart Dresser Bridge, a fixed-span bridge which replaced historic Barrett's Ferry and the former drawbridge.

For much of its distance, SR 5 generally parallels the north bank of the James River, following the path of older colonial roads.

It passes through three of the original eight shires created in the Colony of Virginia in 1634 by King Charles I of England.

Houses and/or grounds are generally open daily to visitors, with various admission fees applicable.

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 18.5 miles (29.8 km) toward Richmond,[3] and was numbered State Route 41.