Route suggestions for crossing KY and Southern IN

[dduelin]

I'm looking at a ride next month to WI to attend LOCSTOC. I'm thinking of crossing the OH river at Madison, IN so looking for suggestions to cross KY on small roads west of I-75 and east of I-65. I'm sort of looking at crossing TN going through Crossville then north on 127 or 27. Eventually back on I-65 as IN flattens out. I've ridden in the hills of Southern IN before but east of 65. Or should I consider crossing the OH River west of I-65? In the interest of time I'll probably be on the interstate once past Indy or Terre Haute. TIA

 

[sTaylor]

I recently explored Highway 150 leaving Louisville into and through Indiana on my way back to Chicago. I found it an enjoyable mix of some twisties as well open prairie and some woodlands.
Safe travels!