Toronto Youth Street Stories is an innovative, web-based storytelling project that was conducted with homeless youths in Toronto. As a collaborative knowledge dissemination initiative, the project engaged youthful participants, authors, community mentors, youth service agencies and university-based researchers. Over 50 youths were encouraged to express their personal perspectives through author-led, creative writing workshops, resulting in youth-created stories, poems and pictures about a wide array of feelings and experiences. Across the dozens of pieces of writing, there is evidence of a chronology of street life, or an “arc of experience”, that ranges from living with abuse and despair, leaving home, living on the street, experiencing a crisis or turning point, accessing services and gradually moving away from street life toward self-sustaining independence and security. This arc of experience includes the stories of youth who have transitioned away from the street as well as those still facing homelessness. This paper describes this arc of experience and illustrates it with the subjective material generated by the youths’ stories about their lives on the streets of Toronto. We conclude that this project provided an important, creative outlet for the youths, and increased understanding of the challenges, stigma and resilience of homeless youth.