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There are many stories about the origins of cyclo-cross. One is that European road racers in the early 1900s would race each other to the next town over from them and that they were allowed to cut through farmer's fields, over fences or take any other shortcuts in order to make it to the next town first. This was a way for them to stay in shape during the winter months and put a twist on road racing. In addition, riding off road in more difficult conditions than smooth pavement increased the intensity at which the cyclists were riding and improved their on the road bike handling abilities.
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