Occaneechee Trading Path, on a map produced by a North Carolina surveyor (who depicted the Fitzwilliam rather than the Dan river)
Source: NCPedia, Moseley manuscript map ("A New and Correct Map of the Province of North Carolina drawn from the Original of Colo. Mosely's")
The Europeans relied most heavily upon the rivers for long-distance travel for several decades. Transportation by water was traditional in England where, "because of heavily indented coastline, no location is more than 125 km from tidal waters."1
Initially, oxen rather than horses were used to pull carts.
one ox-power carts were used for basic transportation in the initial colonial period
Source: National Park Service, An Autumn Harvest (Sidney King painting)
Once they explored inland, even when they did not have Native American guides assisting them, the Europeans followed the easiest routes: the existing trails. The driest trails between the Chesapeake shoreline and the Fall Line followed the watershed divides, the low ridges separating the Roanoke, James, Pamunkey, Mataponi, Rappahannock, and Potomac rivers.
As settlement moved across the Fall Line, the plantation owners required better roads to transport grain to wharves for export to Europe. Road construction, except for bridges and ferries, was managed at the local level. County courts authorized local landowners to determine where public roads would go, and then required landowners to main the public roads that crossed their property. Most traffic was local, and the beneficiaries of the good roads were often the landowners required to maintain them.
unpaved dirt road in Coastal Plain (Surry County)
One farmer did not have a level road to transport his tobacco. Nicholas Taliaferro (pronounced "Toliver" in Virginia...) had to carry his crop to the Rappahannock River, and his address was Tottem-Down-Hill in Culpeper County.2
the road from Henry Hill to the Stone House on Manassas Battlefield
Source: National Park Service, "The Second Battle of Manassas," The Sudley-Manassas Road Looking North Toward The Warrenton Turnpike
before there were car wrecks, there were wagon wrecks
Source: "The Chesapeake & Ohio Railway Directory, Containing an Illustrated History and Description of the Road," Pleasure (?) Travel in the Olden Time (p.298)
wagoneers on dirt roads were able to relax as well as work
Source: "The Chesapeake & Ohio Railway Directory, Containing an Illustrated History and Description of the Road," A Market Train of the Old Virginia Time (p.256)