I participated in Bike the Drive this weekend, and it was a pretty good time. I got up at 4am, hauled my bike onto the Red Line for the trip south, got all registered and then proceeded to ride 30 miles along the lake shore. I have some pretty cool pictures, and the rain mostly held off until the ride was over, but I definately wasn’t ready for 30 miles. The last few miles I was walking up the few small hills and could barely ride the rest. Next time, I’ll pick up the T-shirt before the ride, and get off near my house! 
So, were any other Dopers there that want to share? Anybody have questions?
This is the second year I did the BTD. I enjoyed it a lot both years, though last year it was on Father’s Day. I prefer it later in the year because it gives people more of an opportunity to prepare for it. It has rained so much in Chicago the last few weeks and has been cold on other days, that I really didn’t have much time to ride before Sunday. Luckily, I have riden a lot in the past and have my own stationary bike at home, but I can imagine that many people would have preferred it be later in the year. It would also be nice if they could do it twice a summer, too. Labor day weekend would be nice.
The ride itself is great. LSD is an amazing drive in a car, but is twice as neat on a bike. It was really windy, which is fine when it’s behind you, but a real pain in the ass when it’s front of you. We didn’t have to stop or walk our bikes, but my girlfriend was a bit tired at the end. As you mentioned, it was nice for the rain to hold off until the ride was over - we weren’t sure whether to bring our rain gear, and I’m glad that we didn’t have to.
Overall, it’s a great experience and I only hope that the city continues to do it, and more often.