This report contributes to the knowledge about youth homelessness in Peterborough and provides a local perspective on the factors associated with entrance into homelessness. The report begins with a detailed literature review of the established pathways into youth homelessness in Canada and details the characteristics of the homeless youth population both locally and nationally, as well as the individual, relational, institutional, and structural factors that contribute to youth homelessness. The methodology employed for this research was qualitative, arts-based interviewing that engaged three formerly homeless participants. Participants were asked to use modelling clay throughout the interview to help represent their experiences. Interviews were transcribed and individually analyzed for consistent themes and connections to the literature. This methodology was chosen as a way of generating accessible knowledge of participant experience and providing participants with increased agency in the portrayal of their narratives. A set of key recommendations emerged in four central areas through this research, with more detail provided in the final section of this report.