Oh, definitely Milwaukee...nothing like 14inches of snow shoveling to help you develop your core and force some time off of the bike(and another 4-7 is right around the corner
)
Before the latest weather shift we were riding year round in Milwaukee--there are always enough balmy (30-40F) weekends to let you get out and spin. But the last two years have had so much snow and not enough salt that it takes the fun out of the riding (great big ice ruts). But, Milwaukee has great cycling if you live on the SW (e.g., New Berlin) or NE suburbs (e.g., Cederburg). The roads are relatively quiet, the terrain varied, and there are enough roads to keep you from having to do the same 2 or 3 routes all the time.
That said, I dream of moving somewhere where I don't get all that shovelling "cross training". I really like Tucson for winter vacationing, but I wonder if you lived there whether you'd have enough variety of routes "right out your door" or whether you'd find there was really only one or two because there are only so many roads through the desert.



(and another 4-7 is right around the corner
)
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