Purpose: Previous recreationists-environment interaction studies more focused on how recreationist gets recreation benefit and recreation experience from environment. However, past researches ignored the recreational environment characteristics require recreationists specific ability to perform its function effectively. Therefore, this study adopted the concept of recreationist-environment fit (requirements-abilities fit, needs-supplies fit) and test the relationships among recreationist-environment fit, situational involvement, and flow experience. At the same time, this study also investigates the mediating effect of situational involvement on the relationship between requirements-abilities fit/needs-supplies fit and flow. Methods: A total of 443 usable structured questionnaires were collected from hikers of Yangmingshan National Park in Taipei City, and Shoushan National Nature Park in Kaohsiung City. Data was analyzed by structural equation modeling (SEM). Results: (1) Recreation participants have greater requirements-abilities fit and needs-supplies fit significantly leads to a higher level of situational involvement and flow experience. (2) Recreation participants showed greater situational involvement that also significantly leads to a higher level of flow experience. (3) Situational involvement mediated the effects of requirements-abilities fit and needs-supplies fit on flow experience. Conclusion: (1) The fit between recreationists and their environment can facilitate recreationists’ situational involvement and flow experience. When the recreationists’ abilities are in accord with the environment’s requirements, or the recreation benefits of recreationists are satisfied by the instrumental and expressive attributes of a recreation setting. Recreationists more likely to enjoy the hiking activity and experience pleasure from it, and they temporary feel involvement and experience flow. (2) Situational involvement can enhance recreationists’ flow experience. This result means that recreationists experience positive emotions such as pleasure and enjoyment, so that they fully immersed in hiking activity and loss the sense of time. (3) Requirements-abilities fit and needs-supplies fit indirectly affect recreationists’flow experience through the mediation of situational involvement. The result shows that fit between recreationists and environment will motive recreationists more likely to involve the hiking activity, and enjoy it, and they experience flow.