First of all, I would plead with you not to listen to music out on the bike. You need all of your senses to stay safe.

On the run, you can't beat an iPOD from apple. For $275, you can hold 2500 songs in a case the size of a cigarette pack. I run with it all the time and no way I ever run out (no pun intended) of tunes. You can download songs from the net or from any cd's you own and create playlists like, Brian's 3hr training run, or whatever. Plus it works on both mac and pc. www.apple.com

iPod is cool, and I am a Mac user, but I actually prefer my Rio Sport. They sell one at Costco for $99, and you can get a 256 meg memory card there for $64, which comes out to a couple hours and change of music. Couple nice things about it: No moving parts, very, very light, uses cheap batteries, works with Mac or PC, arm strap, small enough to fit in the pocket of my Ultimate running belt. Mine is maybe a year old, has been beat up pretty good, got soaked in Endurox once, dropped numerous times and stepped on at least once. Still works fine.

I live and die by my iPod. As Clint Eastwood says, "There are two types of MP3 Players: The iPod and everything else."

If you search the web for a while, you can find some gadgets like an arm band to put the iPod in while running.

I run with my iPod all the time! LOVE IT. Here is a link to the apple store to get a referbed one. They are 100% warrantied. If I already did not have a 5 GB one this is where I would buy it.

http://store.apple.com/1-800-MY-APPLE/WebObjects/AppleStore/

After you go to this link, scroll to the bottom left and click on the special deals...I saw an iPod for under $200. Well worth it.

-Trisha

What's a "dock connector" for the iPod? None of the refurbished units include one. How much do they cost and where can they be purchased separately?

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The deeper you get the sweeter the pain. Don't give up the game until your heart stops beating.
--New Order

Not sure. Mine does not have one. Call them and ask.

-Trisha

You might think about a mini disc player. I just bought one and I love it. Much less expensive than an ipod, doesn't skip, plays MP3's, has removable media, and is small. I bought a Sony net MD at Target for $99 and it came with a free armband that holds it and an extra disc while running/biking. You might want to check it out. I just used mine yesterday for a 100km mountain bike race and never heard the same song twice! I even think Sony makes a "sport" version that is water resistant. And as for using it while you bike, I just keep it in my pocket until I am out of town far enough that I don't need to worry much about traffic. Just my 2 cents.

 
The "dock" connector is a relatively recent revision to the iPod line. The first several iterations of the product used only a standard firewire connection. The most recently released models come with a dock -- the ipod connects to the dock via a proprietary connect, and the doc connects to your computer via firewire or USB 2. Advantages of the dock: allows the ipod itself to be a bit lighter & smaller, allows both firewire and usb 2 connections. Disadvantages: proprietary interconnect means if you don't have a dock handy, you're out of luck.

New models described here:
http://www.apple.com/ipod/