There is a need within health, physical education, recreation, dance, and sport programs to increase community engagement via experiential learning. The Chase Charlie Races are presented in this article as a model pedagogical strategy to engage community youths and families in a training program and running event to help promote fitness. Key considerations for conducting a community-based initiative are discussed, such as how to assess project needs, overcome financial and operational challenges, and evaluate the program. An analysis of the benefits for the community and the student stakeholders supports the implementation of this type of program. (Contains 2 tables.)