The past decades have seen an increased interest in understanding how the environment affects population health. In particular, public health practitioners and researchers alike are eager to know how the food environments of neighborhoods, schools, and worksites affect food choices and, ultimately, population risk for obesity and other diet-related chronic disease. However, the measurement tools for assessing the environment and the employed study designs have limited our ability to gain important ground. The field has not yet fully considered the psychometric properties of the environmental measurement tools, or how to deal with the copious amounts of data generated from many environmental measures. The field is dominated by research using unsophisticated study designs and has frequently failed to see the role of social and individual factors and how they interrelate with the physical environment. This paper examines some of the measurement issues to be considered as public health practitioners and researchers attempt to understand the impact of the food environment on the health of communities and takes a broad look at where the science currently is with regard to how the food environment is measured, thoughts on what issues may benefit from more deliberate inspection, and directions for future work.