Research examining border crossing and health has focused on substance abuse, healthcare utilization and air pollution. Living in border communities allows for frequent crossing and exposure to different sociocultural and structural environments. Given high rates of obesity among Latinos and the large percentage living in border communities, it is important to consider the relationship between border crossing and obesity. This study explored the relationship between frequency of border crossing, obesigenic behaviors, measured obesity, and chronic disease. Multistage sampling methods were used to recruit 397 Latino adults living in border communities in South San Diego County. Selected participants completed a face-to-face interview and height and weight measurements. More frequent border crossing was associated with more fast food consumption and a greater reported diagnosis of high cholesterol. Understanding the extent to which border crossing is associated with obesigenic behaviors and chronic disease is important for developing relevant interventions along the border.