There is an update available for the Calendar Printing Assistant so that it will work with Outlook 2010 (the installer says its for Outlook 2007, but it lies, it works with both. :)). In my (very) quick look, there doesn't appear to be any changes, except for Outlook 2010 support.
Download the Calendar Printing Assistant for Outlook
To use the CPAO with Outlook 2013 or 2016, you need to add a registry key to trick CPAO into thinking Outlook 2010 is installed. Note: it will not work with 64bit versions of Outlook. (You can print blank calendars using CPAO).
For a 32-bit version of Office that is installed on a 32-bit version of Windows
String Value: LastProduct
Value data: 14.0.6029.1000
If you don't want to edit the registry, download and run this ready-to-use reg file:
Published July 2, 2010. Last updated on January 29, 2016.