Honestly in Madison you're better off just parking your car on a side road in the residential area and walking around Regent street or hitting up the bars. The stadium is situated kind of strangely where one side is residential and the other side is downtown Madison. There's not really much room for tailgating and you don't see a whole lot of it. Parking is free in the residential neighborhoods, you just have to remember where your car is.
Most of the bars are wide open and grilling brats and stuff. So its kinda like one massive tailgate without the cars.
I'll be there again this year wearing my black and yellow. I've never had a bad time and I've never been punched, but I go with a few Badger fans. Be prepared to take a lot of shit from the students if you walk by their houses. When they do the "jump around" thing the whole stadium feels like its going to implode...its rocking that much. Kind of scared me at first.