Windows 10
Pinning a File to the Start Menu
from PaulC_1 in the Windows Forums
Create a shortcut to the file, and copy that shortcut to the file to the following folder. This is the folder that the start menu reads from.
C:\Users\[username]\AppData\Roaming\Microsoft\Windows\Start Menu\Programs folder
From there: in the start menu, right click on the menu item that appears (probably at the top) and click [Pin to Start]. Alternatively, you can drag the item to the pin space.
Fonts Folder Location
C:\Windows\Fonts