I have a classic iPod and have never had a problem with it skipping. Not sure how it would, really since there's nothing TO skip. I've never tried listening to it while riding, but I do while jogging, which is a lot more bumpy, and I plug it into my car's stereo system with no problems (unlike a CD that will skip on bumpy roads). If you're really concerned, though, get a player with a flash drive (like the iPod Nano, which is also nice and tiny) since it'll have no moving parts to bump around.

Sarah