First time in Kentucky, need some suggestions on what to see and do I’m flying into Chicago on a Friday (in early August) and have to be in Nashville the following Tuesday.  I’ve been to Chicago before, but not Kentucky so I’m looking for some suggestions on where to visit from Saturday through to Tuesday morning.  I will have a rental car.

I’m particularly interested in staying somewhere on the Saturday night that has good bars with live music (rock is preferred, but country is also fine) - but somewhere with a mixed-age crowd (I’m 41 and male).  If it’s a larger city with other things to do then I might also consider staying the Sunday night as well.

Am keen to see some nature on the Sunday and Monday, but really want to be in a larger town (or city) on the Saturday night if possible for reasons I’ve mentioned above.

Thanks in advance!