clipped from: howto.wired.com   
getting your music off an iPod? You'll find that's not so easy.

Apple's iTunes software only lets you put the music onto the player, and not the other way around.

The iPod/iTunes combo was designed with this restriction built in to prevent piracy and illicit trading.

However, there are a number of legitimate reasons you might need to transfer songs from your iPod to your hard drive. For instance, if that fateful day arrives and your PC hard drive crashes, you can restore your music collection without re-ripping dozens of CDs.

Fortunately, there are many applications you can use to get your tunes off your iPod. Some of them are even free

The simplest method for grabbing tunes off of your iPod is also the geekiest. Just enable the "Disk Mode" feature of the iPod from within iTunes, which will allow you to mount the iPod as a hard drive. Then, you can browse the disk using Windows Explorer or the Mac's Finder.

Third Party Apps

Senuti

iPodRip

iPod Access

Anapod Explorer

Podworks

YamiPod