Did you know that during the 1700s that most Kentuckians came from Pennsylvania ports? During this period millions of Germans, Scots and Scotch-Irish landed in Pennsylvania and began their trek to find settlements. The first settlements were in Bucks and Berk Counties before taking the wagon trail southwestward across Virginia, North Carolina and Kentucky. One example is the Boone family. The original settler was George Boone, a Quaker, who resided in Philadelphia with 10 to 12 children. Hinshaw’s Encyclopedia of Quaker Genealogy should help to locate some of the generations. As with so many others, the Boones were explorers and the names of George and Squire reappear again and again in these families. Another source of the origins of Kentuckians is in Maryland. No one seemed to remain in one place during the 18th and 19th centuries. What that means is that the genealogist need to trek along the early explorer path, searching county records and military rosters as Indian troubles were commonplace. Do not forget to research the names of those who served in the militia companies of 1774 when the great Indian war was fought against the Shawnees and Chief Cornstalk at the falls of the Ohio River .
Lord Dunsmore’s War. Irrespective of the fact that the Virginians won the war and a treaty was signed, Cornstalk continued to send his warriors into Virginia and Kentucky to drive out the white man, kill settlers and capture women for slaves. Gutenberg.org has some diaries about women who were taken as slaves. I found an old LWT in Virginia that named two daughters who were taken by the Indians (never returned). This is why you gotta read all the Wills in the counties where your ancestors resided! There is simply a lot of personal information and historical data in these documents.
Also, some extra reading of of history will provide minute details and clues of where to search next.
Kentucky Pioneers.com has a number of old wills and estates online. To learn if any of your ancestors were there, click here