Every year I intend to ride it, but I always snooze out instead. If you like to ride during the daytime, you might like the Boulevard Lakefront tour, which is usually on Father's Day.
For a couple of years in a row, the Grateful Dead played Soldier Field the night before Father's Day. It was fun to see the dazed, waking up deadheads crawling from their tents and seeing thousands of bikes wizzing past them. Maybe they thought they were tripping, and maybe some of them were.