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Although not terribly surprising, it's too bad to read all negative the posts about winter in Wisconsin. This has been a fantastic season for fat biking! I'm pretty sure there's just as many fat bike races as there are XC races in the summer. There are a few choices of trail systems Madison that have groomed fat bike trails in the winter.
There's also the WEMS (endurance mtb) series, which is super fun and laid back, along with big endurance mtb races like Chequamegon 100 and Wausau 24. There's also a bunch of fondo and gravel rides within a two hour drive of Madison. Endless gravel in the Northwoods really isn't too far away.
I'd also say that in Madison, you've got a really strong advocacy culture. There's a ton of bike lanes and paths, and there's always a bunch of bikey events going on.
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