Gamehole Con 6 is coming up soon. I attended last year and it was packed full of gaming goodness. Like most Wisconsin conventions you’ll find a lot of the old guard from TSR days running and playing in games. Last year Ed Greenwood, of Forgotten Realms fame, was there as well.
While the convention is getting bigger, it was well run and organized and still had that small con feel but offered enough gaming for anyone.
I’ll be running some games there this year so make sure to look forward to updates on this site an on Facebook.