Laguna: yes, the BBC usually has an annual Breaking Away ride that involves a roughly 40 mile loop and usually attacts 40-50 participants of all skill levels. Bloomington is now much more beautiful than during the filming- particularly the city square where many scenes take place. A shorter loop is possible including access to a ride on the Little 500 track, the serenade location, the bowling alley, Morgan Monroe Forest, some race locations, locations on the square, their house (still there!), etc...plus, coincidentally, I also have a 280SL...it's just red, not blue.
The quarry is still there...with big "No Trespassing" signs; the owner is very particular because of the drownings that periodically occur there...but it is accessible for the adventuresome! If you search "Empire Mill Road" on google maps, you'll see where it is.
If you have an interest, we can organize a small group to make our own Breaking Away ride...I bet Catrin, and Indysteel and Mr. Indysteel might join as well! Plus, there's just some generally beautiful rides around here!
If you don't grow where you're planted, you'll never BLOOM - Will Rogers