While progressive education has been practiced in formal learning settings for over a century, there is a relatively limited amount of contemporary scholarship on such schools. Acknowledging the nebulous nature of this genre, my study was undertaken to identify the philosophies and practices of a contemporary progressive school. From the conceptualizations found in Kohn 2008's work on the characteristics of progressive educational settings, this project used field observations and interviews to examine the daily work done at a small, independent progressive school in Upstate New York. Taking Pondiscio (2019)'s suggestion that scholars pay more attention to what actually goes on at schools, the study describes the daily teacher-student interaction and ways in which it expresses the beliefs and philosophies of the teachers and setting as one iteration of contemporary progressive education. Case study, narrative, and autoethnographic methodologies were used in considering what is done in this progressive environment. This school was found to be congruent with Kohn's set of descriptors and through the use of a Schoolwide Curriculum and Mixed Age Grouping to also be consistent with existing scholarship on progressive schooling. In doing so they present a set of conceptualizations of teachers, students, and assessment that serve as an example to be considered for all learning settings. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]