A number of Squeakers usually attended the OOPSLA conference each year, including folks from original Squeak Central and the current board.
There was always a Squeak "Birds Of a Feather" (BoF) session on one evening of OOPSLA - traditionally on tuesday evening. At the BoF, a bunch of Squeak/Smalltalk folks gather together and give informal demos/presentations of things that they're doing with Squeak. We usually sign up informally to get a grip on how many presentations there will be.
For some years there was also been an informal "Squeak Bug Fixing Party" at the Camp Smalltalk area of OOPSLA, in which anyone was free to participate. See http://wiki.cs.uiuc.edu/CampSmalltalk/Squeak+Bug+Fixing+Party. Depending on interest such an event might take place again.
