Background: Food insecurity has been shown to be associated with poor dietary quality and eating behaviors, which can have both short- and long-term adverse health outcomes in children. The objective was to investigate the food security status, dietary intakes, and eating behaviors in a convenience sample of youth participating in the Maple Leaf Sports Entertainment LaunchPad programming in downtown Toronto, Ontario. Methods: Youth aged 9–18 years were recruited to participate in the study. Food security status, dietary intakes, and eating behaviors were collected using parent- or self-reported questionnaires online. Results: Sixty-six youth (mean ± SD: 11.7 ± 1.9 years) participated in the study. The prevalence of household food insecurity was higher than the national average with at least one child under 18 years of age (27.7% vs. 16.2%). Dietary intake patterns were similar to the national trends with low intakes of fiber, inadequate intakes of calcium and vitamin D; and excess intakes of sodium, added sugar, and saturated fat. Despite a low prevalence of poor eating habits, distracted eating was the most frequently reported poor eating habit. Conclusions: Although youth were at high risk for experiencing household food insecurity, inadequate dietary intake patterns were similar to the national trends. Our findings can be used to develop future programming to facilitate healthy dietary behaviors appropriate for the target community.