Community supported agriculture (CSA) serves as a platform for local producers, especially for small size farms, to sell fresh, local products directly to its members. CSA is an important approach to promote local economic growth and contribute to sustainable agriculture. Although CSA is widely accepted across the United States, the total number of CSA membership is still very low. It is important to determine the factors that affect the future development of CSA because of its social and environmental benefits. In this study, we analyze how the motivation, barriers, and methods of advertisement influence the participation dynamics of CSA by segmenting consumers based on their past, current, and future CSA participation. Based on a national survey with 795 responses, the results show that the younger generation, high-income families, and people who support sustainable agriculture are more likely to renew their CSA subscription. CSA members are found to be very sensitive to the time of food distribution, the price of products, and the location of CSA farms. Moreover, the impacts of perceived barriers of CSA participation and advertisement method vary based on respondents’ membership status. This paper sheds light on factors that influence various consumer groups and offers a more dynamic analysis of CSA consumer behavior. This analysis enhances understanding of CSA members’ preferences and could help CSA programs expand in the future and to better promote local food systems and sustainable agriculture.