Young people today face a multitude of challenges, especially when growing up in an urban environment. Risk factors such as poverty, exposure to gangs, drugs, and community and family violence threaten healthy development. The positive youth development (PYD) approach attempts to combat these personal and environmental challenges by providing youth with positive, asset-building experiences and meaningful, supportive relationships. There is a need for creative youth development programming that brings these two elements together in a structured and voluntary context, such as a wilderness-based program. This study explored the impact of a PYD program that utilizes mentor-supported wilderness expeditions to build developmental assets among a diverse sample of 159 urban youth in the United States. The Developmental Assets Profile was administered pre- and post-program, as well as 90 days post-program. Quantitative findings show that this type of programming can be an asset-building experience for youth facing multiple risk factors.