I grew up in Minnesota, went to college at Madison, and got accepted to both med schools. Madison is a super fun town and very pedestrian friendly. This is good if you like lots of coffee houses and walking and things like that. That being said, the medical school is a mile or so away from central campus and state street so you are a little more isolated which is not so fun. I was also turned off by the required away rotations...but how you feel about this partly depends on your relationship status.
Minnesota is a bit colder than Madison, if that matters. But then again, Minnesota has all those sweet underground tunnels so the overall coldness x time outside product may be less than at Madison.
Overall, I was a bit more impressed by Minnesota at my visit. This was due to 1) Avoiding away rotations 2) Not liking how far Madison's med school was from the heart of Madison and 3) Wanting a change of scenery.
Either way, good choice!