Sorry to be a party pooper but only time I use my iPOD nano is when I'm on a trainer. I also have iRiver player with FM radio. but that too stays on the trainer.

Road riding for me is still training. (I don't race) but I still train. I'm too busy about riding and all my concentration is on riding. I prefer not to have junk miles in my training.

If you ride leisurly, and you can hear the sound around you, AND you are aware of your sourounding, I see why not.

Besides, if I'm taking it easy, I want to hear the sound of water cascading over rocks, rustling of leaves in the wind, birds singing...