Using multivariate logistic regression, we examined the prevalence and correlates of homelessness among youth enrolled in a community-recruited prospective cohort known as the At-Risk Youth Study (ARYS), between September 2005 and October 2006. Of 478 individuals included in this analysis, 132 (27.6%) were female and 120 (25.1%) self-identified as Aboriginal. The median age was 22 (IQR: 20–24). In total, 284 (56.9%) participants reported baseline homelessness, with most living either at no fixed address, on the street, or in a hostel or shelter. Factors associated with homelessness included public injecting, frequent crack use, experienced violence, having less than a high-school education, and not having been in any addiction treatment. Homeless individuals were at-risk for various adverse health outcomes. These findings indicate the need for additional interventions, including residential addiction treatment, to address homelessness and drug use among youth.