Since the 1980s, the Oxfam Trailwalker has emerged as one of Hong Kong’s most distinctive sports events, challenging teams to traverse a demanding 100-kilometer route along the MacLehose Trail within a 48-hour time frame. Its sustained success in generating charitable funds for Oxfam Hong Kong has not only attracted significant public and institutional attention domestically but also served as a model for comparable endurance events internationally. This edited volume explores the evolution and multifaceted impact of the Oxfam Trailwalker. Drawing on interdisciplinary perspectives in policy studies, public administration, organizational culture, social psychology, and sports sociology, the chapters demonstrate that this event serves far-reaching purposes beyond its philanthropic mandate, encompassing the expansion of international reach, the strengthening of collaborative governance, the fostering of corporate engagement with social causes, and the enhancement of individual and collective well-being. The insights presented in this volume are pertinent to broader debates concerning the revitalization and future development of Hong Kong.