Hacker News.
Python Weekly.
Jessen Oller's, Ian Bicking's and Doug Hellmann's blogs.
@getpy on Twitter, and a bunch of other random pythonistas who'll eventually retweet everything @raymondh says (as they should).
Occasionally skimming the Unofficial Planet Python.
Very occasionally looking at Google Plus communities (although the signal-to-noise ratio in the main Python is way too low in there).
The occasional django-related podcast, although the action in that area is way too fast for me to keep up.
A yearly trip to PyCon UK ;)
Lurking on this list.
Occasionally downloading a new Python release and looking at the changelog :)