The current intense food production-consumption is one of the main sources of environmental pollution and contributes to anthropogenic greenhouse gas emissions. Organic farming is a potential way to reduce environmental impacts by excluding synthetic pesticides and fertilizers from the process. Despite ecological benefits, it is unlikely that conversion to organic can be financially viable for farmers, without additional support and incentives from consumers. This study models the interplay between consumer preferences and socio-environmental issues related to agriculture and food production. We operationalize the novel concept of extended agro-food supply chain and simulate adaptive behavior of farmers, food processors, retailers, and customers. Not only the operational factors (e.g., price, quantity, and lead time), but also the behavioral factors (e.g., attitude, perceived control, social norms, habits, and personal goals) of the food suppliers and consumers are considered in order to foster organic farming. We propose an integrated approach combining agent-based, discrete-event, and system dynamics modeling for a case of wine supply chain. Findings demonstrate the feasibility and superiority of the proposed model over the traditional sustainable supply chain models in incorporating the feedback between consumers and producers and analyzing management scenarios that can urge farmers to expand organic agriculture. Results further indicate that demand-side participation in transition pathways towards sustainable agriculture can become a time-consuming effort if not accompanied by the middle actors between consumers and farmers. In practice, our proposed model may serve as a decision-support tool to guide evidence-based policymaking in the food and agriculture sector.