Have you heard of the KAT (Kentucky Adventure Trail) ???
Here are some words of wisdom from Jeff of the Quad Squad located out of Crestwood, KY.
And I quote Jeff himself... "This is a 833 mile loop (not counting the hard sections) around the hills and mountains of south eastern Kentucky. It is about 65% rural narrow twisty paved roads with the rest being gravel and dirt roads. It will take 4-5 full summer days of driving to complete the main loop. It will take 5-6 days if you take the hard sections. Some of these areas are very remote so do not go alone! The average distance between gas stops is around 50 miles. I have marked with waypoints the gas stations, food and hotels.
This loop does go through some active coal mining areas on the far eastern side but the roads are still open to the public. You may run into a situation where the road is shut down due to work or blasting. There will be a security guard in a truck, the ones that I have spoke with are very friendly and more than happy to tell you a way around.
As far as vehicles go, the main loop can be done in fairly stock 4x4's but keep in mind there are sections with rocks, some mud and hills so I highly recommend that you have experience in these conditions and run an aggressive tire.
If you decide that you want to take the hard sections, I highly recommend lift kits, rear locker and at least 31" aggressive tires. Mud, creeks, hills, off cambers, rocks, tight switch backs, downed trees and lots of other trail nasties will be traversed. I would only recommend taking these sections if you are a very experienced off road driver."
A fantastic ride report by Cannonshot... http://www.advrider.com/forums/showthread.php?t=971478another great report with pics by Mudaura...
A fantastic ride report by Cannonshot... http://www.advrider.com/forums/showthread.php?t=971478
Another great report with pics by Mudaura... http://advrider.com/index.php?threads/high-water-kat-ride.1060895/