This is a proven method of synchronizing an Outlook calendar with an Android device. Google Calendar Sync will sync the Outlook calendar with Google Calendar and the Android device will also sync with the Google calendar, wirelessly. Once set up, the synchronization is automatic - set it and forget it. Google Calendar Sync will support both the 32 and 64 bit versions of Outlook 2003-2010. I have personally used this solution with no difficulties in setup or function.
I do recommend this software if it meets your needs and requirements. The link below will take you to a site that has easy to follow directions for downloading, installing, and configuring the software.
http://cellphoneforums.net/motorola-droid/t304785-sync-motorola-droid-ca...
For more information on Google Calendar Sync, you can visit Google here:
http://www.google.com/support/calendar/bin/answer.py?answer=98563