I have never found this calender helpfull.
I think instead of doing that, tweaking the existing feature will do.
You can tweak the Email Notifications and add a dropdown menu to select the frequency. It can be a month, a week, a day or when every new contest has been added. (With the upcoming contests option)
New contests cannot be found out with the calender, cause you cannot know when a contest will be added from before.
And frequently checking the calender stuff, who has the time to do it?
When the upcoming contests are already being shown in the contests page.
You do realize that Toph already sends email for upcoming contests. 
But, yes, we don’t send out email for all contests.
I have probably spent enough time around here to realize such things (I think). 
