chukker65, the three ways I have tried are using Palm Desktop, iCalTextImport, and iCalSyncNUTD.
The first two take a lot of work if you want to preserve all your categories as separate iCal calendars. iCalSyncNUTD is simpler, but I found it messed up repeating all day events among other things.

Thank you for replying to my post. I think that is amazing that Now, Apple, iCal, Entourage, Outlook etc. have no way to work together in support of iPhone. I had to stand in line to get one yet now I have no way to keep a calendar. My calendar changes often and it's a group calendar with about 10 categories and covering 7 people's appts, I think I need to just wait until a developer develops something that actually works. You are wonderful to tell me how to do this but it just seems like too much to do on a weekly basis.

I AM STILL OPEN TO HEAR ABOUT OTHER SOFTWARE OUT THERE! I wonder if Google Calendars can do any better?

Thanks for placing this here too! I'm about to try a little of this since I want to do the whole .mac-cloud thing with my NUDC calendar. I actually got on the forum to post this "cart before the horse" request or reminder that I think NOW products deserve a native space on the "cloud basket" of apps! Then I would be in heaven too. --stan