This qualitative study investigates self-described democratic educators' conceptions of the core qualities of democracy, democracy in education, and their claims to educating students in and for critical participatory or Longschoolhouse democracy. Data was collected from an experienced and diverse sample of ten educators, one Haudenosaunee Elder, and secondary and primary sources which examine the nature and practice of democracy, and democracy in education. This thesis argues that the participating democratic educators' philosophies of democracy, democracy in education, and claims to democratic practice reveal both possibilities and obstacles for the realization of Longschoolhouses. I have concluded by identifying a number of catalytic and telling areas for future research, including the need for a curriculum of biophilia or the love of all life forms in educational philosophy and practice, the possible influence of educational experience on educators' conceptions of democracy, and the influence of personal experiences of oppression and discrimination in framing and forming educators' conceptions of, and practice of democracy.