Background/Objectives: Puerto Rican households often face elevated rates of food insecurity. Frequently, households experiencing food insecurity turn to federal and emergency nutrition assistance for urgent or prolonged aid. This study analyzes factors influencing food insecurity and food assistance program involvement among Puerto Ricans in Holyoke, Massachusetts, amidst the COVID-19 pandemic. Methods: Using a combination of community-based participatory recruitment, purposive sampling, and web-based tools, we collected 284 survey responses. Our paper employed Pearson’s chi-square, logistic regression, and hierarchical linear models to assess relationships between demographic and household attributes and food access outcomes. Results: Variables such as having children in the household and age significantly influenced food relief participation and food insecurity outcomes. Puerto Rican heritage and low educational attainment were strong predictors of obtaining federal food aid. Low-income participants disproportionately faced food shortages and depended on emergency food initiatives. Our findings indicate that demographic and household factors significantly influence food insecurity and accessibility. Conclusions: Our study demonstrates that the pandemic made it challenging for households to obtain consistent, safe, and affordable nourishment. The impacts were unequally spread; hence, Puerto Rican communities and low-income groups were most affected.