The following needs to be done (Not necessary in this order for your Outlook calendar to sync up with your Droid phone)
1. Set up your Google email account on your Droid.
2. Install Google Calendar Sync on the desktop or laptop you use to access your Microsoft Outlook.
Here is the Google Calendar Sync link - http://support.google.com/calendar/bin/answer.py?hl=en&a nswer=89955
3. Make sure your calender on your phone is configured to work with your Gmail email address. You can specify this under your Phone Calendar Settings.
4. It may take a few minutes to sync, but that's it!