This study sought to clarify the lifestyle and physical and mental health status of homeless people in a cold region of Japan. 28 participants who visited a soup kitchen completed the physical health check-up and questionnaire surveys in 2017. Five were invited to participate in semi-structured interviews in 2018. Mental health was evaluated using the General Health Questionnaire-28 (GHQ-28). The results revealed that a high proportion of homeless people did not consume enough food. Their meat, fish, and vegetables intake were limited, indicating that inappropriate eating habits may affect physical health. Furthermore, four people consumed meals once or less every two days, and all of them were living on the street. In addition, 18% (n = 5) answered that they often consumed alcohol in the daytime, and 68% (n = 19) had a total GHQ-28 score above the cut-off point (>5). In this regard, among those with a GHQ-28 score of >5, seven drank in the daytime even though they consumed meals once or less a day. Indeed, qualitative results revealed physical and psychosocial distress experienced, including limited access to food, anxiety for the future, lack of social support, and erosion of self-esteem. These findings suggest that restrictions on food selection due to financial insecurity, alcohol issues, and mental disorders may impact the food intake and subsequently lead to deteriorating physical health and living on the street may also significantly impact mental health among the homeless. which are helpful for health and social workers to develop necessary interventions targeted at this population.