Migrate Apple Calendar to Outlook

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Open the Calendar/iCal application on your mac
Click the File menu then choose Export > Export.
In the Save As box, type a name for the calendar you wish to export. Note that the Apple application often has separate calendars for Work, Home, etc. You will need to click on each calendar you wish to move.
Select a location on your hard disk to save the file.
Open Outlook for Mac.
Click the Calendar icon.
Locate the exported calendar file(s) you just saved.
Drag them one by one to your Outlook calendar.