This pilot study was conducted to explore the associations between stressors related to homelessness and modifiable health risk factors (poor diet, insufficient physical activity, and overweight/obesity) and to provide direction for future research. Participants (N = 57) were homeless adults enrolled in a smoking cessation program. Analyses were conducted to characterize the sample as well as the relations between relevant stressors (discrimination, chronic stress, and fear and mistrust) and health risk factors. Inadequate daily consumption of fruits, vegetables, and fiber was common. High-fat diet and insufficient physical activity were also prevalent, and the majority of participants were overweight/obese. Participants commonly endorsed discrimination, fear of victimization, mistrust of others, and several other stressors. Greater endorsement of stressors was associated with a high-fat diet. Results suggest that lifestyle interventions and policy changes may be warranted in homeless shelters to attenuate the potential effects of stressors on high-fat dietary consumption among smokers.