I totally agree with what roaminggnome said. You need to transfer your old iPod to computer at first,and then try to connect your computer to new iPod via USB cable or other tool.
Maybe this column of [iPod Transfer Backup|http://www.softwarebbs.com/wiki/IPod_Transfer] can do you a big favor. What it described that can help iPod users to transfer iPod to computer, iPod to iTunes, iPod to iPod or iPod to iPhone and so on.
I ever used this software to solve the same question, that is Aiseesoft iPod to iTunes Transfer, automatically transfers your iPod and iPhone music, video, playlist, photos back to PC and iTunes. With this iPod to iTunes Transfer, you can backup all your music and video in a couple of clicks.Maybe you can visit this website to see more information:
If your songs are purchased from iTunes store, Plug in iPod to computer, then go to iTunes menu "File-> Transfer purchases", It will copy your bought songs from iPod to computer.
Or You may refer to this guide, it will show you the detail steps to transfer files from iPod to computer or iTunes, including music, video, playlist, photo, etc. It's easy to understand and works pretty well for me.
Hope it helps. Email me if you need further help.