A work vehicle automatic traveling system includes a route element selecting unit that, on the basis of state information, sequentially selects a next travel route element on which a work vehicle is to travel next, from a travel route element set and a circling route element set. The route element selecting unit includes a cooperative route element selection rule, which is employed when a plurality of work vehicles carry out work travel cooperatively in an area CA to be worked, and an independent route element selection rule, which is employed when a single independent work vehicle among the work vehicles carries out work travel independently in the area CA to be worked. When the independent work vehicle is carrying out independent work travel in the area CA to be worked, and a work vehicle aside from the host vehicle is carrying out circling travel based on the circling route element or is stopped, the next travel route element is selected on the basis of the independent route element selection rule.