Is it possible to restore songs from an iPod to iTunes? I have a 160 GB iPod Classic and a Windows 7 desktop with iTunes containing roughly about 13,000 songs. My external hard drive containing all the songs crashed but I managed as long as all the songs' file names were in iTunes and when the iPod syncronised with iTunes, the songs remained on the iPod. Recently I had my computer reinstalled and iTunes was formatted and wiped clean, now if I sync my iPod I know my iPod will be wiped clean as well.

So is it possible to recover songs which are there — on the iPod — but not in iTunes or the desktop?
There is no end to the people that will offer to sell you some software to do this.

Here is a long list:
https://discussions.apple.com/docs/DOC-3991

There should be several free ways to do this including this one:
http://download.cnet.com/PhoneTrans/3000-18553_4-75736709.html

Many advertising free downloads but are crippled and will only allow a few songs at a time.

I don't use windows so I cannot recommend one or the other but I would not pay for something you can find for free if you just look a little bit.

Good Luck