There used to be an awesome online game where your challenge was to gerrymander constituencies. I had great fun and it was amazingly education. God knows what it was made in, possibly a Java Applet. I wonder if anything exists with modern tech.

Edit: It was this - http://www.redistrictinggame.org/game.php

It looks like someone has made one here though: http://gametheorytest.com/gerry/game/