Problem

I recently noticed at work in my Microsoft Outlook 2003 SP3 the holidays are no longer showing up in my calendar beyond the year 2007. My initial re-action was to just re-install the holidays into the calendar by going into the menu Tools -> Options -> Calendar Options… -> Add Holidays…, selecting United States and Canada then clicking “Ok” three times. However this did not resolve the problem just made it some what worse for the fact that now all my holidays in my calendar for the years 2007 and less was duplicated.

Solution

1. Open your Outlook Calendar
2. Menu, View -> Arrange By -> By Category
3. Select all the listed holidays that is within the “Holiday” category and then delete them by pressing the delete key.
   Be careful not to mark anything you created manually.
4. Now re-install the holidays by going into the menu Tools -> Options -> Calendar Options… -> Add Holidays… and then select the countries you wish to see the holidays for.
5. Click “Ok” three times.

At this stage you should now see the holidays beyond the year 2007 all the way until the year 2012. If you wish for the holidays to go beyond the year 2012 you can manually edit the outlook holidays file with a text editor located at “C:\Program Files\Microsoft Office\Office11\1033\Outlook.hol”. If you can’t find it there do a search for “Outlook.hol” or “Outlook.txt”. Outlook 2000 and older has it stored in a file called “Outlook.txt”.

Source: Outlook Tips – Missing Holidays
Holidays File: Outlook 2003 Holidays File with Family Day Included for Saskatchewan