I received a Nuvi 255 as a bonus for renewing my auto club membership recently. When I registered the unit, it downloaded a heap of stuff from the website including software to allow for planning trips.
Unfortunately, the next day, my Beta Windows 7 started giving me the "2 hour shutdown" treatment so I went and purchased a full copy and installed it as a clean install. I'll just download all that stuff from the Garmin site again, won't I!
Guess what? Now I've lost all of the stuff that downloaded and can't seem to find it on the Garmin site again.
You should be able to download the web updater software. This software should automatically recognise your gps model and download the updates required.