But often the first hunters themselves stayed and grew up as farmers and landed proprietors.[8] Many of the earliest pioneers, including most of their leaders, founded families, which took root in the land and flourish to this day, the children, grandchildren, and great-grandchildren of the old-time Indian fighters becoming Congressmen and judges, and officers in the regular army and in the Federal and Confederate forces during the civil war.[9] In fact the very first comers to a wild and dangerous country are apt to be men with fine qualities of heart and head; it is not until they have partly tamed the land that the scum of the frontier drifts into it.[10] In 1776, as in after years, there were three routes that were taken by immigrants to Kentucky.

One led by backwoods trails to the Greenbriar settlements, and thence down the Kanawha to the Ohio;[11] but the travel over this was insignificant compared to that along the others.

The two really important routes were the Wilderness Road, and that by water, from Fort Pitt down the Ohio River.

Those who chose the latter way embarked in roughly built little flat-boats at Fort Pitt, if they came from Pennsylvania, or else at the old Redstone Fort on the Monongahela, if from Maryland or Virginia, and drifted down with the current.

Though this was the easiest method, yet the danger from Indians was so very great that most immigrants, the Pennsylvanians as well as the Marylanders, Virginians, and North Carolinians,[12] usually went overland by the Wilderness Road.