This study describes three collegiate programs that have a high interest in creating engaging learning environments outside of the classroom. The three settings in this study are a three-year degree granting college focusing on internship-based learning, a nationally recognized service-learning program at a private university, and a small private college emphasizing work and service. Research was guided by two exploratory questions: (1) How can students, faculty, administrators, and community partners’ work together to create engaging learning experiences? (2) How can students feel empowered through experiential learning programs? Three themes emerged as important aspects of experiential programs that foster engagement and empowerment: learner autonomy, accountability, and peer support. These features are discussed and presented as important components to experiential learning programs.