Well, it's the wrong direction but Madeline Island (La Pointe, WI on Lake Superior) 4R5 is a great destination in the upper midwest.
Drinks at Tom's Burned Down Cafe, score a night at Woods Manor (
www.islandelegance.com), take the ferry over to Bayport to enjoy the view and grab some food.
Door County, Wi is supposed to be real pretty like.
Milwaukee is a blast. Fly into to Timmerman (KMWC) take a cab downtown, go mini-bowling at Koz's Mini Bowl on the south side, lunch at the Hi Hat on Bradey St. and drinks just about anywhere.
Between OSH and ATL? Yikes. Chicago maybe?
Hannibal Missouri is a surreal river town and the Mark Twain museum is sorta interesting if you're in to that sort of thing. Lots of oldster tourists, ice cream parlors and about a zillion references to Becky Thatcher. Airport is just north of town and a cab ride is a few bucks.
Stopped there once for an overnight taking a 172 from the Twin Cities down to Mississippi and that was enough. But hey, at least I can say I've been there. I wouldn't go out of my way to get there though.
Stop in St. Louis and check out a Cardinals game, drink Bud and eat ribs or something.
Good music in Nashville, I hear.
