This study explores the phenomena of the Black Mountain College Semester (BMCS) as a means to locate the spirit of progressive education in the 21st Century. Through interviews with contemporary faculty who organized and participated in the BMCS, along with document analysis of texts related to the history and legacy of the BMC, this research seeks to identify effective strategies for cultivating innovation, creativity, and community in the classrooms of today and tomorrow. Using a thematic analysis of interviews and historical texts, this study illuminates the values that past and present educators hold as sacred, and the ways in which they put those values into practice in their classrooms. Findings illuminate persistent tensions between descriptions of optimal learning conditions, and the realities of the highly-structured nature of higher education. Specifically, a tension between academic structure and freedom was prominent along with an acknowledgement of the significant impact Information and Communication Technologies are having on our on all aspects of contemporary lived experiences. This study carries implications for the ways in which institutions of higher education, and the educators working within, go about establishing innovation, creativity, and community as values.