According to Yahoo blogger Christopher Null: The Working Guy

Reader George writes: I lost my songs from my hard drive and want to download the songs that are on my iPod into another hard drive. Is there software that can pull the songs from an iPod to a hard drive?

There sure is. In fact, there's a lot of software that will let you back up your iPod or copy songs from your iPod back to your PC in the event of a hard drive crash. The catch: Virtually all of it costs 20 bucks to use. That's unacceptable considering bilateral music transfers should have been built into the iPod from day one. Why should we have to pay extra to circumvent Apple's inane DRM? (The other problem: A lot of this software doesn't work as advertised or hasn't been updated recently. A number of online lists of iPod backup software you'll find are hopelessly out of date.)

Fortunately, after a lot of hunting I found one solution which is free and works well: YamiPod.

YamiPod stands for "yet another iPod manager" and it's a quick download for Windows, Linux, or MacOS. You don't even have to install the software. Download the executable and it runs from anywhere (so you can drop it on a thumbdrive and manage your music from any machine).

YamiPod is actually better than most of the iPod backup tools because it is more than a one-off program that simply copies files from your iPod to your PC: It's a full-fledged music manager that you can actually use in place of iTunes. Operation is pretty similar to iTunes on the whole, though the design is a little different and obviously you can't purchase tracks from the iTunes Store with it.

Of course, the killer feature is being able to get songs off your iPod. The feature isn't all that easy to find, actually, so here's how to do it: After plugging in your iPod and looking at the list of music, in the left pane select all the artists on the iPod, then in the bottom pane select all the music on the device. Right-click and choose "Copy song to..." from the menu. Choose your options then click Destination to decide where to put the music and click Copy to get started. If you have a large library, expect this to take several hours.

If you prefer to use iTunes, you can then re-import the songs into an iTunes installation and start fresh from there.

LINK: YamiPod