Cumberland Falls is beautiful, if you go a little further through the woods there's a much-less-crowded, much-less-littered spot called Eagle Falls, beautiful swimming water and climbing rocks, wild blueberries growing there in the summer, check it out if you get the chance. I'm planning to hit up Red River Gorge later in the summer...
Some solid radical folks were running a place called the village trough in Berea for a while, but that got closed down, not sure what they're up to now but I'm sure they're still around, and that town has a good number of openminded people generally... In Lexington there's some rad people supporting/organizing w strikers who are picketing a factory called Trane.
Oh. In the hills in east KY, there's this woman named Linda, she's got a bunch of land called Beyond Yonder, tucked in the woods down a road called Hell For Certain. Basically there's no way to not get lost, so you have to stop and ask people, "do you know how to get to hell for certain?"
So they have these great little festivals at Beyond Yonder every fall, lots of good people and travelers come through, and if you can get in touch with Linda or ask around, they might be having gatherings earlier in the summer too, I don't know. Check it out if you can! Give people my love from the green mountains!