An easy-going lakeside college city with many quirks and amenities, Madison is perhaps Wisconsin’s most appealing moderately sized city. The State Street region is the main artery of Madison, pretty much connecting all noteworthy attractions. This stretch is highlighted by Capitol Square at one end and the charming University of Wisconsin grounds on the other. The campus area is known for its common college eccentricities, beautiful, clean fields and multifaceted community contributions. And of course, on fall Saturdays, football.

Madison is oddly configured. Perched on an isthmus (or a sliver of land between two lakes) it is nearly encapsulated by water. Mix this with over 200 local parks and you have a nature-laden, darling of a town. And if that’s your thing, check out any of the smaller communities and state parks that adorn southern Wisconsin. Other noteworthy attractions are the Unitarian Meeting House, designed by Frank Lloyd Wright, The Chazen Museum of Art and other local visual art galleries, the engaging farmer’s market and various other architectural and natural comforts.