I'm planning on a 4-5 day getaway in July. Did Lake Superior last year, have done the Dragon, Mount Rushmore. Looking for tasty roads within a reasonable distance of South Bend/Chicago.
Requirements:
* Interesting things to see
* Entertaining roads
* Preferably north to maximize daylight and minimize temps
Thoughts? Suggestions?
I would suggest following the curvy road and let the interesting things come to you as you pass them by...who knows what you'll find?
If you want north...then maybe southwest Wisconsin into Cheeseland between LaCrosse and Prairie Du Chien on the west, and Hollandale and Hillsboro on the east. Curvy roads, Cheese, curvy roads, beer.
If you don't mind the Ohio, WV, Kentucky area...I would head straightaway to SE Ohio and do a nice loop based out of Athens, Marietta, or Caldwell. Then I would head east and travel through WV for a day and end up in Elkins or pictured Rocks area. Then I would meander south and base out of Lewisberg. If you have more time, meander even further south and base out of Tazewell or Marion, VA.
Get yourself a nice Gazetteer...the map will tell you where to go.