In this article, I use data collected from research conducted in the summer of 2001 at the Grass Roots Arts and Community Effort (GRACE) in the Northeast Kingdom of Vermont. I present case studies of artists with developmental disabilities, who along with other isolated groups, are considered to be Outsider Artists. I begin the article by defining this term as it is understood and defined by the art world. While this label is expedient and the participants of GRACE fall within this label, I suggest that the socialization found in the GRACE workshops is atypical of Outsider Art, and thus requires that we think more deeply about this label. Later, I discuss how the interaction between the staff and participants raise questions about teaching and learning, and suggest that public education has something to learn from this interaction. (Contains 6 footnotes.)