As noted in the last post, before Kentucky was a "state", it was a "county" of Virginia. From 1776 to 1780, it was called "Kentucky County". It certainly has a long, long history.
"Chickacoan" was the "Indian District" which it belonged prior to 1648. It became "Northumberland" (VA) in 1648 having received many folks from the English Civil War. In 1651 it became "Lancaster Co."... then "(Old) Rappahannock Co." in 1656... then "Essex Co." in 1692... then "Spotsylvania Co." in 1720... then "Orange Co." in 1734...then "Betetourt Co." in 1770...leading to "Fincastle Co." in 1772. It was out of Fincastle Co. that Kentucky County was formed 1776, lasting until 1780. The years between 1776 to 1780 were a difficult time for the folks in this new county of Virginia.