Long-distance collective walking is a popular activity in cities across China. However, related research is limited, creating a research gap to explore participants’ dynamic experience and related influential factors. Therapeutic mobilities theory explores the relationships among walking, health, and well-being from a qualitative perspective. Based on therapeutic mobilities theory, following a systematic process, this study develops a scale to quantitatively estimate the perceived environmental, personal, and social factors that may influence health and well-being. By applying construal level theory, this paper further hypothesizes that personality traits and familiarity moderate environmental, personal, and social perceptions. Data were collected with a paper survey (n = 926) from the “Shenzhen 100 km Walking” event. The findings highlight that long-distance collective walkers have comparatively greater experiences of health and well-being in three aspects: positive social interaction, individual development, and environmental understanding. Personality traits, familiarity, and gender moderate this well-being experience. Theoretical and managerial implications are discussed.