Recent research has shown multiple motives for high-risk sport participation derived from research on adult participants. The aim of this study was to provide insights into motives and risk-related aspects in adolescent high-risk sport participants and to compare those findings with adults performing the same activity. Semi-structured interviews were conducted with 24 adolescent (14-20 years) freeriders (skiers/snowboarders who ski outside the protected areas of a ski resort) and 24 adult freeriders (26-41 years). A content analyses was done using MAXQDA software. Both cohorts reported the motives Challenge (adolescents: 92%, adults: 88%), Freedom/Pleasure (adolescents: 88%, adults: 75%), Friends (adolescents: 88%, adults: 79%) and Balance (adolescents: 63%, adults: 63%). However, the description of friends differed between adults and adolescents. Whereas adolescents mostly referred to a community and shared interests, adults described the importance of trust and the development of deep friendships through the activity more often. Nature was a major motive in adults (83%) but not in adolescents (29%). Most of the adults have already experienced a major accident or close call (n = 19; 79%), contrary to adolescents (n = 7; 29%). Adolescents learned about the risks in freeriding primarily through their families (n = 10) and the ski club (n = 9). Some adults reported to have realized the risks involved in freeriding after starting with the activity due to experienced negative outcomes. Both cohorts were largely motivated by the same motives. As the new generation of freeriders seems to receive more instructions about risk reduction, it might be interesting to see if this educational approach results into less accidents or close calls in this group.