The ride is scheduled for 9/20. Here's an itinerary Grayson, Mark, and I came up with.
Chicago - Fort Royal (VA). 2 days. 710 miles. Overnight stop: Mansfield (OH).
Fort Royal (VA) - Roanoke (VA). 1 day. 230 miles.
Roanoke (NC) - Cherokee (NC). 1 day. 350 miles.
Cherokee (NC) - Chicago. 2 days. 710 miles. Overnight stop: Louisville (KY).
Total: 2,020 miles. This is rather aggressive schedule. It would be nice to do at least some sightseeing. Some of us have never been in this part of the country. Also, several club members expressed interest in touring the Bowling Green Corvette Assembly Pant. Here's one potential route.
Cherokee (NC) - Chicago. 2 days. 740 miles. Overnight stop: Boling Green (KY).
Howard, Grayson, John and I met on Thursday and reviewed the route as well as other issues related to group riding, lodging, navigation, gear, etc. So far so good. Four of us are mostly on the same page. The only issue I'm not sure about is if everyone has the same definition of staying on schedule. The proposed schedule is tight. Any deviation from the route for sightseeing or for any other reason will add another day to the trip.
There's another meeting scheduled for Tuesday, September 16th, to go over the list again.