Getting to this new land [what was to become Kentucky] was some kind of chore. The New River (Wood's River) offered a pathway to the west, but gave all kinds of trouble to those who were on the other side of the mountains. All these mountains stood in the way. For many years, the Blue Ridge Mountains seem to be the greatest barrier. Once over these, there were the Shenandoah Mountains separated by a valley area that gave a little brake to the mountains. Then came the Allegheny Highlands that seemed to go on forever into the distance. What were these poor folks along the coast to do?
The drawing to the right shows the general idea about these mountains. The "Blue Ridge" in blue, the "Shenandoah" in purple, and the Cumberland-Allegheny Highlands in green are outlined. The river road is again shown in orange, and one can get a sense of why those folks above the mountains [PA, NY, etc.]would find the river route a much better avenue. The folks from VA, NC, and MD would have to figure out another way perhaps...coming round the mountains.