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My favorite long running route is the North Branch bike route. It begins in Caldwell Woods at the corner of Devon and Caldwell and meanders north to the Chicago Botanical Garden. Distance is 21 miles, perfect if you are training for a marathon or ultra. It is an asphalt path with a crushed stone path next to it. I have been within 10 feet of deer on two occasions in the last couple of months. One problem during the winter is that the forest preserve district does not clear the path of snow.