In the aftermath of Hurricane Katrina, a synchronistic set of events and relationships generated a new kind of experiential learning in communities across Mississippi. Educators based at the University of Mississippi, community-based educators, social justice advocates, and funders collaborated to provide the resources and opportunities for diverse groups of Mississippians to participate in the Circle of Trust[R] approach as a vehicle for community healing and transformation. Created by educator and public intellectual Parker J. Palmer and the Center for Courage & Renewal (www.couragerenewal.org), this approach is a retreat-based learning format founded on a set of principles and practices that honor the cultivation of one's own wisdom and voice and evoke the courage to integrate the inner life with the active life of service and leadership. This chapter explores how utilizing the principles and practices of the Circle of Trust[R] approach helped to lay a generative foundation for democratic education in service of community healing and transformation in Mississippi.