Some of the info here is dated, but much is still good. http://buckyville.yuku.com/topic/8428/Visiting-Madison-for-a-football-Saturday#.VGvdtWdNdRE
There is no official "tailgating" lot, but a lot of UW lots, business lots, and private citizens selling space. To tailgate, get there early. Otherwise, I'd hit a bar on Regent Street pregame and walk up to a tailgate (I'd avoid student-aged groups) with some beer, say it's your first time in town for a game, and if anyone would like to talk college football. Chances are you'll be given some more-than-decent beer and a chance to chat.
There's usually something in the Fieldhouse for the last game, which might be OK if it is really cold.
There is no official "tailgating" lot, but a lot of UW lots, business lots, and private citizens selling space. To tailgate, get there early. Otherwise, I'd hit a bar on Regent Street pregame and walk up to a tailgate (I'd avoid student-aged groups) with some beer, say it's your first time in town for a game, and if anyone would like to talk college football. Chances are you'll be given some more-than-decent beer and a chance to chat.
There's usually something in the Fieldhouse for the last game, which might be OK if it is really cold.