Dotty Dumpling’s Dowry (317 N. Frances St., 608/259-0000, 11 a.m.–1 a.m. daily, $4) always wins local surveys for burgers, which really are sublime creations (if a bit pricey). Some Madison radicals frequent the place simply because the owner put up a Pyrrhic battle against the city when it wanted to buy his former location for the city’s new arts district.
The Great Dane (123 E. Doty St., 608/284-0000, 11 a.m.–11 p.m. daily, $7–16) is a brewpub occupying what was Madison [1]’s landmark Fess Hotel. The interior upstairs is fairly spacious, but it’s best known for its great courtyard. The catacomb-like downstairs is a great place for moody swilling. The Great Dane has been ranked in the top 10 brewpubs in the nation in terms of beer consumption; no surprise in a university town in Wisconsin. The food is exceptional, way above basic pub grub, and the place has got a new billiards hall and cigars for aficionados.
It’s nearly raucous inside, but stick the brats, burgers, and other pan-Wisconsin-produced fare at 
The Old Fashioned (23 N. Pinckney St., 608/310-4545, www.theoldfashioned.com [2], 11 a.m.–9 p.m. Mon.–Fri., 4 p.m.–1 a.m. Sat.–Sun., $5–28) on china on a white tablecloth and it’d pass for fine dining. It’s my fave restaurant to take out-of-towners.
Links:
[1] http://www.moon.com/destinations/wisconsin/madison
[2] http://www.theoldfashioned.com