Carefully constructed field-based experiences in teacher education programs have been recognized as one of the essential conditions for effective teacher learning. Most college/university-based teacher education programs, however, are still dominated by the epistemology that academic knowledge is the authoritative source of knowledge about teaching, while spaces outside the college classroom remain the "practice fields." This study examined Project CONNECT (PC), an after-school program designed to create early experiential learning opportunities for pre-service teachers (PSTs) by bringing together different aspects of expertise from the schools, communities, and universities. Pre-service teachers in this study worked with children one afternoon a week in school-based sites during their sophomore and junior years. Case study was adopted to assess the impact of the experience on teacher learning and the factors contributing to the effect. Multiple data sources, including weekly reflection journals, field observation notes, and an exit survey were collected and analyzed. Results revealed participants' transformation of professional identity, and development of professional skills and dispositions. Several factors emerged as important to PSTs' learning throughout the experience, including connections between the course and the program, quality of faculty supervision, and systematic reflection. Implications for teacher education were discussed.