What are some good routes to take from Boston to Indianapolis. Each of the past three years, my girlfriend and I have driven out on Memorial Day weekend to see the Indy 500 with her mother and stepfather. We have stuck to the interstates in the past, but this year it might be nice to get off the beaten path and make the trip a little more interesting.

This past year we took a detour up to Chicago and Madison, WI. I lived in Madison for a summer and I wanted to show my girlfriend why I liked that place so much.

I'd like to make the trip to Indy in 3 days probably. In the past we have done the drive in no more than 2 days and a couple of times we did the drive in a single swoop of 16 hours driving.