Population: 228,775
Median Home Price: $218,000
Why it’s on our list: Wisconsin’s capital city may have truly horrible winters, but the “cheeseheads” make up for it by packing more into summer than just about anyone else. “Mad-town” is a big city and a college town at the same time, which creates a fine balance of work and play. The city is built on an isthmus between two expansive lakes, which means there’s always a place to swim. Madison also has some of the most challenging yet quiet roads in the Midwest just a few miles west of town.
Live here if: You’re looking for Berkeley,Calif., mixed with Chicago.
Don’t live here if: You hate being pestered to sign some progressive group’s petition while you shop for groceries.