We take a yearly trip from WI to Destin FL and enjoy finding areas along the way to visit. Previously we've done St. Augustine, Hilton Head and Highlands, NC. We've stopped at Berea, Bardstown and Lynchburg and really enjoy the area. This year we're planning on making Richmond, KY our base (free nights at the Hampton Inn).
Searching some previous posts and the KY tourism website I've gotten a few ideas. We want to hit a few locations on the Bourbon Trail (have already seen Makers Mark and Jack Daniels), do some hiking (Natural Bridge looks terrific) and anything else.
I'll also take restaurant advice for that region. We prefer local to chains which may be harder to find as we're driving.