8 days, where to go?

Hi, I am a Jerseygirl with 8 glorious days to travel and explore between festivals. I leave Dublin, Ohio on a Monday morning, and next place I have to be is Milwaukee, Wi, 8 days later. I was thinking up to UP of MI, but where to go, what to see? We cant go into Canada since we r traveling with commercial goods and the paperwork would be rediculous. We like pretty places with nice day trips, flat hiking, little towns. Ideas anyone who has been to that area?Do I wing it or get reservations? Thank you all in advance.