This mixed-methods study addresses the relationship between the availability of food and realized food access by studying the retail food landscape of Holyoke, Massachusetts – a small, socio-economically diverse city. While a large body of empirical research finds that low-income communities and communities of color are especially likely to lack adequate access to healthy foods and experience increased vulnerability to food insecurity, few studies explore urban food environments through a mixed-methods case study approach. Through the use of food store mapping, store audits, and resident interviews, this research is a nascent attempt to articulate how the unique development histories and cultural politics of urban neighborhoods affect food access. The analysis finds that local food environments in Holyoke vary by social and spatial context. The study further considers how health and stability of a community is affected by the distribution and variety of food retail stores. In particular the study articulates the constructs of race and class in the food environment via the spatial mismatch of preferred food stores, mobility challenges, and the role of small urban food stores in the context of Holyoke’s foodscape. Implications for local food security policy are discussed.