Use
Chocolatey and install the packages
Chocolatey GUI and
Calibre.
From the Chocolatey GUI, you can quickly list the packages installed, those with an update available, and install the update of all these in 1 click.
Note that it generally takes 24 hours for the new version of Calibre to be available in Chocolatey (package is managed by a third-party user, not by the Calibre developer, not a problem just that take a little time).