My apologies, I just didn’t see EE4 in the question title, so yes the code will be very different.
You are sort of in the right place with the EEW_Upcoming_Events.widget.php file. It is certainly the one that outputs the dates.
To make the changes you need though, it would require modifying a function called espresso_list_of_event_dates, which is found in the core/helpers/EEH_Event_View.helper.php file.
This is a pluggable file so can be copied to a custom plugin or to your theme’s functions.php.
Modifying this requires more assistance than we can provide in support, it really needs a developer to look at it. I spent some time examining it and to get it to do what you want will require an hour or more, or someone more skilled than I!
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