Retire as a Cheesehead? News | May 15, 2025 | 0 | by Morgan McCarthy Madison is one of the top 25 best cities to retire in 2025. That’s according to a new report by Forbes, which compares more than 950 cities based on metrics like home prices, healthcare access, and walkability. The study puts Madison in the top 25 due to its good air quality, medical services, and favorable tax treatment for Social Security.