The area around Madison is interesting. New Glarus is is an area with Swiss heritage and the renowned New Glarus brewery. South of there, Monroe is known for Limburger cheese and home to the old Huber brewery, now run by Minhas along with a distillery. To the west you have Mount Horeb and Mineral Point, scenic small towns, along with Dodgeville and Frank Lloyd Wright's hometown, Spring Green. Near Barneveld is the Botham winery. All of these are in the Driftless area, a scenic region similar to the Ozarks. And since they cater to tourists, you'l find a number of craft brewpubs because, well, Wisconsinites love to imbibe.
North of Madison is Wisconsin's most popular tourist region, Baraboo near Devil's Lake and Wisconsin Dells. Sauk City and Prairie Du Sac are across the river from the state's best-known winery, Wollersheim, founded by Agoston Haraszthy in the 1840s before he continued west and became the father of California viticulture.
All these towns are within an hour of Madison, which has plenty of eating and drinking attractions of its own. In addition to it being the state capital and home to the University of Wisconsin, it also has an unusual feature in that its downtown is built on an isthmus.
Of course there's plenty to see and do in and around Milwaukee and Door County as well.