Rogaining is an orienteering running sport where participants need to decide what control points to visit and in which order. The objective is to collect the largest possible score associated with the visited controls, without violating the time limit. While extensive literature exists on the orienteering problem from a participants' point of view, there is limited understanding of how to design a rogaining contest where physical abilities do not dominate over cognitive skills in influencing the race outcome. To create these contests, we propose a heuristic bilevel optimization approach where at the upper level organizers assign scores to candidate control points, while at the lower level participants solve the classic orienteering problem. The simulation of the selected courses by the participants results in a provisional ranking that allows to evaluate the score assignment as determined by the organizer at the upper level. We apply our methodology to the 2023 World Rogaining Championships, demonstrating the necessity of thoughtful score allocation to ensure a balanced emphasis on both skills.