The opportunities, challenges, and lessons of the pilot phase of a community development program in a small liberal arts college are presented and conceptualized in this paper. We based this program on an experiential learning model derived from Paulo Freire's critical pedagogy and Stephen Brookfield's notion of critically responsive learning. A high value is placed on students' participation, as their increasingly community-based learning enters into a fruitful dialogue with classroom knowledge and readings. Their experience of being both learner and teacher in a trusting, collaborative classroom community prepared them for their field placement. The qualities of resilience and adaptability to new needs and knowledge, modeled by their professors in class, become part of the template for their own community experiences. The qualitative data come largely from student accounts drawn from their course projects, field trips, and community journals and from the evaluations of and by the eleven participating students. (Contains 2 footnotes.)