Bowling Green here. You've got the eastern version of Garden of the Gods available in southern IL, the Ohio River right near town, and then driving east, you've got the karst areas and then into the Appalachian foothills. Headed south, down through Hoptown and Russelville, there's the shaker town and farm fields, then Kentucky and Barkley lakes. Kentucky has more miles of navigable waterways than any other state in the US, so plenty of creeks, rivers, and lakes to check out.
Of course, you can head further east down to Cumberland Gap and Deal's Gap, or up the Lexington for the horse farms. There are plenty of rackhouses and distilleries in central and eastern KY, too.