Contemporary artist residencies are institutions or programs that enable artists to develop their practice beyond the confines of their typical work setting. Increasingly, they are also a means to access significant material, interpersonal, and professional resources, and a medium through which to engage with local communities. In response to these developments, the present interview-based study aims to understand how artists develop within a community context by investigating the work and experiences of eight artists who have participated in community-based residencies across—and sometimes beyond—the United States. By collecting each artist’s narrative and supplementing it with documents, images, and auto-reflections of their artwork, the study investigates the complex network of characteristics that help facilitate the creative process. Furthermore, by canvassing research from fields like social psychology, business management, and arts education, it explores the relations of educational reciprocity that emerge between artists and residency communities. This study suggests that the complex physical and interpersonal dynamics of each residency environment contributed in distinctive ways to the artists’ development. It also notes that each unique residency program provided support for the use of new materials, the exploration of new practices, and the investigation of new content. The residency characteristics that were most conducive to creative growth included (1) difference from one’s typical working environment; (2) access to new (and sometimes unconventional) materials, tools, and facilities; (3) social opportunities such as shared meals and public forums to cultivate relationships with residency cohorts; and (4) ample time (usually 1–2 months) and space (access to both private and public studios) to settle into the residency environment, explore one’s artistic practice (and the practice of other resident artists), and foster relationships among cohorts, staff members, and community visitors. Ultimately, this study argues that artist residencies can contribute to the field of non-formal art education by serving as a relational framework for artists and their residency communities.