We've put on several beer tasting mini-festival type events with pro brewers and homebrewers both pouring, typically split evenly amongst ~20 booths. It is a charity event, with a $30 suggested donation, and all proceeds go to charity. Open to the public, with fliers distributed far and wide, and has never been a problem.
Sounds like you're planning something bigger, but if its on your own land, that may make it even more straightforward.