My best cycling moment would be the second year I did Ride Around the Bear. Previous year, I did and was happy to complete it without having to pull over and puke. Second year, my goal was to shed an hour off my time. I did take off 58 minutes. Would have been an hour but on one of the last turns, I made a bad shift and my chain popped of. Took a couple of minutes to get it back on!
Oh well I did it in 7:40 total time and 7:05 ride time. Was #123 out of the 400. Was great to be a 220lb clyde and beat a bunch of skinny people at their own game!
Second best is when I upgraded the components on my Cannondale to Dura Ace, built my own wheels and the bike has been perfect since! Nothing is better than gliding down the road, looking down between my legs at the sparkling spokes and thinking to myself,"Yeah, I built these MOFO's"!