Rachel Winston Rippy (1930-2019) was an artist and educator dedicated to the philosphy of self-directed learning. She was born in Antwep, Belgium and emigrated to the United States in 1942. From 1964-1968, Rippy, along with her husband Wilbur, taught at the Fifteenth Street School, a free school in New York City founded by Orson Bean influenced by the Summerhill School in Suffolk, England. The Fifteenth Street School was based on the pedagogical principle of self-regulation, emphasized creativity and exploration, and classes were voluntary. Rippy later worked at the Bank Street College, advising and leading workshops for other teachers. The Rachel Rippy Collection on the Fifteenth Street School (dated 1944-early 2000s, bulk dates 1964-1968) consists of materials created and collected by Rippy documenting her and her husband Wilbur's work as teachers at the school. Materials in this collection include photographs in multiple formats, drawings by students, and original stories by students, many of which reflect current events of the time period, such as the Cold War and the Apollo space program. In additional to materials created at the time of the school's operations, this collection also includes notes, research, and writing used in the creation of the self-published 2019 book Voices of Children: The Story of the Fifteenth Street School. The collection documents not only the operations of the Fifteenth Street School, but the wider educational aims and objectives of the free school movement of the 1960s.