Brad Williams and I organize a (mostly) monthly Philadelphia metro area Meetup. We cover a variety of topics and generally split the group into two rooms so that our users can pick a topic more relevant to them.
Generally speaking, we host a "beginners" and an "advanced" session, with topics such as "how to deploy your first WordPress site", "intro to plugin development", "getting started with the Genesis framework" and, this past Meetup, even a collaborative development of a new BuddyPress-powered site that will hopefully take over a lot of the news and discussion functions from the Meetup site itself.
Pizza and soda is served each month and we do occasional giveaways (Brad always has a few WordPress-related books to give out, for instance, and our hosts give away training classes).
The BuddyPress site I mentioned is at:
while the Meetup page is:
We meet at Future Media Concepts (FMC) Philly, between 3rd & 4th on Chestnut, generally on a Wednesday, almost always from 7-9pm, and will head out to a local pub for a beer and conversation after the Meetup is over.
We really have a vibrant group and average between 30 - 40 attendees each month.