Non-traditional settings, such as schools, early childhood education programs, and healthcare clinics, can play a critical role in preventing obesity by providing free and nutritious food outside of food pantries to households that are experiencing low or very low food security, particularly during emergency situations. This evaluation study describes a low-income population that attended free food and produce distribution events during the COVID-19 pandemic. In 2021, a cross-sectional survey was administered to this group (n = 1498) to assess their food security status, fruit and vegetable (F+V) consumption, and prevalence of chronic disease condition(s). Program and event assessments were carried out using descriptive, bivariate, and multivariable logistic regression analyses. More than a quarter (26%) of the participants attended the free food events for the first time. Approximately 70% reported some level of low food security, 57% to 64% did not meet F+V intake recommendations, and 37% had a diet-related chronic disease condition. In the adjusted models, households with very low food security had lower odds of meeting F+V recommendations (aOR, 0.41, 95% CI, 0.28, 0.58 and aOR, 0.27, 95% CI, 0.19, 0.39, respectively) and higher odds of having a chronic condition (aOR, 3.49, 95% CI, 2.34, 5.20) than those with high or marginal food security. Given these experiences, future research should examine how safety net food assistance programs can incorporate alternative service/distribution models to improve the nutritional value of the foods they offer.