Recreational activities are uniquely suited for the implementation of a positive youth development (PYD) approach, as they create space for youths’ physical, psychological, and social development. This may be especially true for vulnerable youth who face additional risk factors such as single parent homes and living in low-income communities. Momentum Bicycle Clubs (MBC), based in Greenville, South Carolina, use noncompetitive recreational bicycling as a mechanism to facilitate group mentoring opportunities for high-risk youth. MBC engage youth with their community while providing opportunities for leadership, building positive relationships, exercise, and learning new skills. This exploratory project’s purpose is to better understand the bicycle as a PYD mechanism through group mentoring by studying MBC program design, processes, and outcomes. Researchers identified three primary themes that indicated the bicycle provided youth opportunities to gain responsibility, confidence, and improved health. Sub themes provided additional context. For example, youth gained responsibility for their bikes and related equipment, as well as their individual and the group’s safety. MBC is an example of using individual specialized recreation equipment as an effective PYD mechanism that allows the program to meet more PYD desired outcomes than traditional programs. The bicycle rides differentiate the program dynamic from other PYD programs as the mentors are also group participants. This allows the mentors to share in the experience and role model behavior, which may foster stronger group identity and cohesiveness. Year-round asset intensive programs of this nature have management challenges, including sufficient resources (e.g., bicycle storage and maintenance), mentors willing to ride bicycles, as well as ensuring youth safety while riding. The resource challenges are met through extensive partnerships with government, nonprofit, and commercial agencies, which has also benefitted the program through a wider variety of mentors, adult role models, internship opportunities for the youth, and community knowledge about MBC. Safe bicycling is accomplished through extensive training, locating the clubs in areas with access to low traffic streets, and a 20-mile paved multiuse path. Lastly, since it is difficult to have meaningful conversations while riding, mentors must build in time before and after rides and at planned stops to facilitate the most meaningful mentor-mentee relationships.