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Virginia-Kentucky Boundary
From here:
The Virginia-Kentucky state boundary involved less conflict and less debate than the other boundaries that now exist between Virginia and North Carolina, Tennessee, Maryland, and the District of Columbia.
In 1776, the General Assembly divided Fincastle County to create Washington, Montgomery, and Kentucky counties. The name Fincastle disappeared, since it honored the family of Lord Dunmore at a time when he had fled from the developing American Revolution in Williamsburg.
The straight line of the Virginia-North Carolina boundary and the twisted boundaries of two natural features - the Big Sandy River and the Cumberland Mountains - were used to define the edges of the new county called Kentucky:
All that part thereof which lies to the south and westward of a line beginning on the Ohio, at the mouth of Great Sandy creek, and running up the same and the main or north easterly branch thereof to the great Laurel Ridge or Cumberland Mountain, thence south westerly along the said mountain to the line of North Carolina, shall be one distinct county, and called and known by the name of Kentucky.


