My family is from letcher county. Burleys are good to start imo. You will probably want something with a high nic content, coming from cigs. Cornell and Diehl make a few good strong tasty burleys.
If you are quitting cigs you’ll want some high nicotine blends, anything Burley from Cornell and Diehl, maybe some Virginias (GL Pease Union Square and Capstan Blue Flake are good ones). Grab and english blend or two as well. Peterson Nightcap and Seattle Pipe Club Plum pudding are good options.
There is good advice here on tobaccos you might try. My suggestion would be to pick 2 or 3 and then settle and get acquainted with your pipe. It can be a little frustrating at first.
You have doubtless already discovered there is a wealth of info here from people who started out just like you.
Happy smoking my friend!
Welcome from Illinois. A few years ago my wife and I stayed at a couple of Kentucky's state lodges... Dupont Lodge Cumberland Falls (Corbin) and Hemlock Lodge Natural Bridge (Slade). We also spent time visiting Red River Gorge, Lexington, Louisville and Mammoth Cave. Kentucky is a beautiful state...we'll be back.