It's a good question! I think it might be helpful if we expand the time frame, however, from 1795 to 1850. More people will be interested and you might pick up some valuable resources.

Carrie Eldridge has produced some specialized map books that I've found very helpful. She describes the trails and rivers and migration routes to/from the river, etc. She has a whole series, including one specific to this area. I've just moved, and mine are still packed away...but I think you can google her name and come up with the titles.

My ancestors [Finical and Ramsay/Ramsey] moved down the river, first into Kentucky from Pennsylvania, after 1820. The siblings then split up and went on into Ohio and Indiana.

All best, Darlene C. Joyce, CG, Minnesota