Bicycles have been useful transportation tools for many years, and have recently become more popular in terms of leisure and health. Increasingly, people choose regular cycling activities as a means of becoming healthier and happier. However, the relationships between why people choose to cycle, what benefits they get from bicycle-based leisure activities, and how their wellbeing is improved have not been fully explored. In this article, the relationship between cycling motivation, leisure benefits, and well-being is examined. Specifically, internal and external factors are considered in the motivation to cycle. Leisure benefits comprise physiological, psychological, and social benefits, while well-being consists of life satisfaction, self-confidence, and self-affirmation. A questionnaire survey is developed, and field data collected in China. A descriptive analysis, correlation analysis, and regression analysis are conducted. The results show that leisure benefits are positively affected by cycling motivation and both cycling motivation and leisure benefits have a positive impact on well-being. The practical implications of the results of the study are also discussed.