Informed by Progressive education reforms of the nineteenth and twentieth century, progressive movements in librarianship, the social responsibility movement within the American Library Association (ALA), and recent collaborations of ALA’s youth-focused divisions, the authors link historical precedents with current examples, ideas, and practices to inform initiatives in education and literacy programming. Progressive librarians and educators share a history of common goals. The article explores how these histories connect with current examples of interinstitutional collaborations among educators, school libraries, public libraries, universities, and community organizations. This paper traces Progressive librarianship to Youth Community Informatics (YCI), collaborative programs in which public libraries, school libraries, teachers, community organizations, and universities connect to form new services or teaching models that connect learning to life in an integrated way. These programs are developing innovative approaches to teaching students; promoting literacy; and encouraging critical thinking and community connectedness within schools, libraries, and community contexts.