Increasing research has focused on the built food environment and nutrition-related outcomes, yet what constitutes a food environment and how this environment influences individual behavior still remain unclear. This study assesses whether travel mode and distance to food shopping venues differ among individuals in varying food environments and whether individual- and household-level factors are associated with food shopping patterns. Fifty neighbors who share a traditionally defined food environment (25 in an unfavorable environment and 25 in a favorable environment) were surveyed using a mix of close- and open-ended survey questions. Food shopping patterns were mapped using Geographic Information Systems (GIS). Stores visited were beyond the 0.5-mile (805 meters) radius traditionally used to represent the extent of an individual’s food environment in an urban area. We found no significant difference in shopping frequency or motivating factor behind store choice between the groups. No differences existed between the two groups for big food shopping trips. For small trips, individuals in the favorable food environment traveled shorter distances and were more likely to walk than drive. Socioeconomic status, including car ownership, education, and income influenced distance traveled. These findings highlight the complexities involved in the study and measurement of food environments.