The agricultural sector in South Holland is highly productive and contributes greatly to the economy. However, current industrial agricultural practices generated several severe environmental and socio-economic challenges. Various renowned international institutions have emphasised the necessity for a radical, rather than an incremental, transformation in the agri-food system. There are growing calls to shift the paradigm from industrial agriculture to agroecology. Agroecology is a fundamental alternative vision of the agri-food system, bundling the power of sustainable farming practices that utilise ecological principles and re-establish the connection between farmers and consumers, and by extension nature. This study sets out to introduce the reader to agroecology and to discover strategies for how the province of South Holland can stimulate the transition to agroecology. To achieve this goal, the research methodology comprised a literature review and semi-structured interviews with agroecological farmers, an agroecology expert, and a provincial agricultural policymaker. The results uncovered that the underlying goal of the agri-food system should be transformed from profit and production maximisation of industrial agriculture to sustainability and social justice of agroecology. Achieving this goal shift requires fundamental changes and will be a tremendous challenge because of the complex and embedded nature of the agri-food system. Agroecology simultaneously tries to realise this transformation on three fronts: as a science, a set of agricultural practices, and a movement. Furthermore, the research identified key barriers and enablers in the transition to agroecology in South Holland from the agroecological farmers’ perspective. The province of South Holland could stimulate the transition by providing long-term affordable land, revising regulations to support forward-thinking practices, adopting an integrated approach to agriculture, bridging the gap between civil servants, farmers, and consumers, restructuring subsidy allocation, and lobbying to simplify (organic) certification processes. The research verifies the results of previous studies on several barriers and enablers but distinguishes itself by focusing specifically on the farmers’ perspective and the province of South Holland. Additional research is needed to broaden the scope beyond the viewpoint of agroecological farmers, and how to implement the policy recommendations effectively. Currently, the Dutch agri-food system is not yet ready for a paradigm shift from industrial agriculture to agroecology. However, the system is being pressured from various angles generating windows of opportunity. While being just one actor in the agri-food system, the province of South Holland could stimulate the development of agroecology by incorporating agroecology explicitly in policymaking.