To be honest, a lot of the challenges and stuff we find out through word of mouth. I have taken part in NaNo Prep Challenge since 2008, so every year since then, and I knew about it from hanging out on scroll and I'm familiar with the ones who run it. I also volunteer and judge a round in it. So, then I tell others about it who show signs of interest in nanowrimo before October starts.
The 52 stories thing is something that has been discussed in the chat rooms that are available here on WDC. A few members got chatting and decided to give it a go. It's also linked to a group they started but they got people to join by talking about it.
There are items on WDC to advertise contests and activities, so some find information in those two places too. But much of it is by word of mouth (or typing as it were on here).
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