Nice idea!

For Mr.'s general area....the Hilly Hundred near Bloomington IN. It's 50 miles each day of the weekend. It's pretty popular and has maybe 5,000. But it didn't seem too congested. Nothing compared to running the Chicago Marathon.

http://www.hillyhundred.org/GenInfo.html


However the Kentucky ride that Mak mentions look great and actually it's about the same distance from me. Maybe we can do BOTH.