Note that there is a trail north to the Ohio River, along the Little Sandy, originating near presentday Grayson
What appears to be an early Midland Trail travels west through Grayson to west of Olive Hill where it splits,
with one branch going to Flemingsburg and the other to Mt. Sterling. Mt. Sterling was a significant Native American
burial mound site ("Little Mountain", the "Mt." part of "Mt. Sterling), so we may assume that was the reason for
the original trail to pass through that area. The easterly portion of the midland trail may not have Native American origins.
Many of the pre-European trails followed natural water courses, which are generally north-south in this part of Kentucky.
The location of Mud Lake ("Mud L.") appears to correspond to the present location of Cave Run Lake.
An historic Native America trail followed the path indictated, from the Mt. Sterling area, through Cave Run Lake (since flooded)
to the present day Morehead area. "20 Licks" (near presentday Olive Hill) is an interesting notation.
I couldn't find a way to download the entire map of all Kentucky, but it can be browsed at this link:
Here's another interesting early map (1795), courtesy of Jon Hagee