First off, good for you for setting some lofty goals. Always nice to have something to work for. But a word of advice on the 5 Boro Ride: be prepared to walk more than ride. I tried it for the first time last year and HATED it. Far too many people that don't know how to ride in a group. Either you were dodging people who randomly stopped for no reason, or you were getting buzzed by some kids trying to fly through the crowd. And then you would just stop for 5 or 10 minutes, slowly inching forward. We never rode smoothly for more than a few minutes, and I was very tense from worrying about people crashing into me. We actually had to stop about halfway as in 4 hours (in the rain) we'd only gone 17 miles Plus at one of the many stops a guy came up beside me and tipped over onto me, thereby knocking me over and onto my brother. My front rim got bent and I was really annoyed. I've heard that if you skip the official start and pick up the course near the park, it's a lot better. I wish someone had told me these things, that's why I'm giving you a heads-up.