The following blog lists a VB Code sample for a yearly planner style calendar. It reads your default Outlook calendar and creates a HTML calendar. Supports up to 12 months. Code can be adapted to filter out categories.

http://niveauverleih.blogspot.com/2007/05/yearly-calendar-view-for-outlook.html 

I tested it with Outlook 2007 and it works great. You can create a 1 -12 month calendar and print it, email it, or publish it to the web.

Tip: if the code fails on this line:
Attribute VB_Name = "YearlyCalendar"
Comment the line out (add a ' at the beginning) or delete the line.