The popular pilgrimage to the 88 temples on Shikoku Island, Japan associated with Kobo Daishi (774-835 A.D.), the founder of the Shingon sect of Buddhism, is a large scale representative circular pilgrimage covering some 960 miles. The changing nature of how pilgrimages to the 88 sacred places are made and how rituals are conducted at each sacred site reflects Japanese cultural preference. Behind the dynamic process is the self-organizing "mechanism" to resolve conflict through compromise. While modern modes of transportation have increased the speed with which the pilgrimage can be completed, the traditional walking pilgrimage is still considered to yield the greatest religious merit. Conflict between the attainment of religious merit and finite externally imposed time restraints symbolizes the larger set of incongruities associated with the increased physical pace of life in securalized societies and the yearing for the security of some sacred absolute. The resolution of the conflict between religious merit and convenience has been sought in a variety of areas including the way in which the pilgrimage can be made(order of temples visited, segmentation of the total pilgrimage system, establishment of miniature pilgrimages, acceptance of modern modes of transportation) and how the rituals are performed at each sacred site. Exploration of conflict resolution through the examination of the roles plays by pilgrims, pilgrim leaders, priests, area residents, transportation providers and government bodies reveals the underlying strength of the ongoing popularity of this Buddhist pilgrimage and the complex nature of the self-organing system that has evolved over the last three centuries.