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
Once they explored inland, even when they did not have Native American guides assisting them, the Europeans would have followed the easiest routes: the existing trails. The driest trails between the Chesapeake shoreline and the Fall Line would have followed the low ridges, the watershed divides separating the James from the Paumkey, Mataponi, Rappahannock, and Potomac rivers.
As settlement moved across the Fall Line, the plantation owners required better roads to transport large hogsheads of tobacco to wharves for export to Europe. The county courts required landowners to main the roads that crossed their property. Most traffic was local, and the beneficiaries of the good roads were the ones required to maintain them.
Once counties were established, the county courts assigned responsibility for maintaining certain stretches of roads to nearby landowners. Their tithables were required to work several days a year to keep roads in good repair. The House of Burgesses recognized that settlement in the Shenandoah Valley would require county governments to handle such local operations, and authorized the creation of two counties west of the Blue Ridge in 1738.
Today's I-81 and the earlier Route 11 parallel the Blue Ridge and transect Virginia, notheast to southwest. The original settlers did not construct their roads straight to Tennessee, however. Many of the early settlers moving to the cheap lands south of Virginia migrated through Southside before the Wildrness Road was constructed south of the New River. They crossed to the east side of the Blue Ridge through the gap formed by the James River, or at Maggotty's Gap (between Roanoke and Boones Mill in Franklin County). Some Scotch-Irish moved from the Shenandoah Valley to Southside, and then kept moving to more-distant frontiers as English settlement streched westward. For example, William Bean was in Augusta County in 1742, but four years later he was in Lunenburg... and in 1768, he may have been the first Englishman to settle in Tennessee. 2
Morgan Bryan, a Pennsylvania Quaker, invested three months of his and his sons' labor to improve the trail over Maggotty Gap in 1748, before leading a group to found Bryan's Settlement on the Yadkin River. The Moravians used that same route on their trip from Pennsylvania to start what is now Winston-Salem, and in the late 1830's the Franklin Turnpike was constructed to connect Danville with Fincastle in Botetourt County.3 Daniel Boone's family followed that route to North Carolina, before he blazed the trail to Cumberland Gap and into Kentucky.