Every time I attempt to print a calendar using the Assistant it prints one 
page and then stops.  I have tried to print multiple pages of a weekly 
calendar and each time it prints one week and then stops.

I love the layout and colors of the calendar but I can not get more than one 
weekly calendar to print no matter how many weeks I select to be printed.

Calendar Printing Assistant is known to be quirky.  It works best with
Outlook 2007.

I cant say i know a fix for your issue.  However, if you cant work
around for this issue or you need a better printing solution, consider
using a addin for MS Office called Wincalendar instead.  It converts
Outlook Calendar to native MS Word and Excel format - and supports
printing multiple weekly pages.  Works pretty but it is not free (free
to try).  For screen shots & more info see:
http://www.wincalendar.com/calendar-maker.html