Pros: So bike friendly it's almost scary, home to many custom bike builders.
Cons: Chicago-style winters, a lot of Treks.

In a sense, Madison is the cycling Detroit, only without the bankruptcy. There are plenty of custom framebuilders that make their home in or around Madison (including Waterford and Ellis Cycles), and slightly larger bike company Trek is actually based in Madison itself. What this means is two things: 1) Plenty of bike advocacy, and 2) This is where you want to be if you're looking for a job in the industry, or just catch sight of prototypes before Interbike. And if you're just getting into cycling, they have a bike share setup AND a bike rest stop. Not to mention a dedicated website.