A number of Squeakers usually attend the OOPSLA conference each year, including folks from original Squeak Central and the current board.
There is always a Squeak "Birds Of a Feather" (BoF) session on one evening of OOPSLA. At the BoF, a bunch of Squeak folks gather together and give informal demos of things that they're doing with Squeak.
We usually sign up informally to get a grip on how many presentations there will be.