1. Mammoth Cave National Park
One of the more liberal cities in Kentucky, Lexington is a nice stopover if you’re in the area. Healthy food options and some historical areas. Lots of horses and related activities in Kentucky if that’s your thing. If you’re a rock climber, the very popular Red River Gorge is not far, with plenty of cheap options for accommodations. Miguel’s Pizza for example has sparse $2 camping spots. The gorge is pretty regardless of the rock climbing. Very foresty with some streams. I camped the night, but the weather was rainy and there had just been record flooding in the area so I didn’t get to much unfortunately. Not too far is Cumberland Falls State Park with a pretty massive stream and waterfall that offers a nice picnic stop en route to Lexington if you’re coming from the south. Also nearish is Big Bone Lick which is home to a group of bison and houses remnants of ancient mammoths. A neat stop if it’s on your way, but I wouldn’t go out of my way to visit.