Google the overlook restaurant in Leavenworth, IN. Make sure you take 135 through brown county, then after you stop and eat take 37 through Paoli, IN. One of the best rides the state has to offer, and the restaurant is cool.
Have to plan your fill-ups on that route because the gas stations aren't to close together. I like to take SR 62 from St. Meinrad up to Sulphur and go south on SR 66 down to Cannelton. Then once I get to Spencer county it is all county roads.