I don't wear an iPod when I ride. I would really like to, because certain music will definitely make me ride faster and harder, but I'm just too paranoid to do it. I like to be able to hear others on the trail (my music would drown out a bear bell), and more importantly, hear rattlesnakes. Seems like everywhere I ride has them. Just because you can see them on the trail doesn't mean they aren't there, right next to you as you ride by within striking distance. Fortunately I've only heard them, but have yet to have an encounter. I've only seen sweet natured garter snakes.

IF I used headphones, I would put loud, angry stompy music on it! LOL