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Organizing a racing event is not an easy task. Organizing a racing event that spans across multiple days and whose participants have to run (on foot) for 100 miles is even harder. In such events many checkpoints are needed to provide runners with access to food, water and, if necessary, medical assistance. At these checkpoints updates on participants' health status and race timings need to be sent to a central location so that followers across the globe can monitor the overall progress of the race as well as the current situation of individual racers. This paper examines development challenges and presents a flexible open source solution for a web-based software application, EnduRan, z that we created for managing long-distance racing events. The paper takes a closer look at the need for this software application and gives details on the application's specification, design, and implementation. Design guidelines resulted from this software project, together with several lessons learned from it, are described as well in the paper. Results of using EnduRan in the 2009 and 2010 Lake Tahoe 100 Miles Endurance Races and pointers to future work are also included.