The rapid transformation of the agriculture system in the United States over the course of the twentieth century has continually challenged farmers to adjust and innovate to survive. In North Carolina, in recent decades, tobacco farmers have been forced to mechanize, diversify, or transition their farm operations. Interestingly, most tobacco farmers that have chosen to continue farming have opted for the less profitable grain and livestock industries instead of pursuing fruit and vegetable industries, which can match or exceed the income per acre from tobacco production. Research on this topic has covered the processes behind the declining tobacco industry, begun inquiring into the challenges of the fruit and vegetable industries, but has stopped short of a full evaluation of the farmer's decision making process. Through the use of in-depth interviews, this research focuses on understanding the decision making processes of small tobacco farmers that have transitioned to fruit and vegetable production. Findings reveal three major factors driving farmers to fruit and vegetable production: farmer dissatisfaction with the tobacco industry, involvement with farmer advocacy organizations, and the appeal of fruit and vegetable production. Two major challenges for this transition are the farmer's strong ties to tobacco and a range of marketing obstacles. This study has identified several major ideas that require more research but may serve as a tool for governmental and non-governmental farmer advocacy organizations: fruit and vegetable production systems can be made more viable by focusing on increasing marketing outlets per farmer; urbanization plays a significant role in the ability of farmers to access land and to access markets and customers; and other agricultural regions with major crops and the range of public health implications, can learn from this case study.