, Abstract: Background: The aim of this present study is to explore what makes orienteering meaningful and rewarding to former elite athletes’ years or even decades after ending their elite careers. Methods: Applying a qualitative approach with a case study design, data was collected through semi-structured interviews with 11 former elite orienteers from Norway and Sweden, and the data was subsequently analyzed with thematic analysis, resulting in two main themes: individually matched challenges and a social community. Results: The character, structure, and culture of orienteering both enabled and encouraged former elite athletes to make the transition into recreational sport. Even so, the characteristics of the sport related to both its structure (range of ages, level, and ambition) and organization (well-organized) as well as the participants’ backgrounds (well-educated) and intrinsic motivation (satisfaction, enjoyment, mastery) seemed to match a lifelong sport participation. Conclusions: These factors could indicate that orienteering is a sport that can facilitate a lifelong sport participation for athletes with such a background.