Agroecological food system transformation remains marginal in South Africa despite numerous policies, plans and programmes favouring sustainable agriculture. Problems of weak budgets, fragmented interventions and lack of coordination reflect the power dynamics in the prevailing food system, dominated by large-scale conventional agriculture and agribusiness. The paper provides an in-depth case study of the importance of promoting agroecological transitions. Following a qualitative research methodology based on a literature review for context, preparatory discussions with local contact points, and semi-structured interviews and focus group discussions with local actors in the field, the paper describes, analyses and characterises the agroecological transitions in the Overberg District in the Western Cape. It considers the broader policy, discursive and organisational landscape of agroecology followed by an in-depth analysis of the site drawing on key informant interviews and focus group discussions. The results demonstrate that local stakeholders are positioned to better connect food and nutrition issues with human health, biodiversity, climate change, natural resource management, and local development. As a result, transformative dynamics could emerge from local projects and programmes. Several lessons and recommendations are drawn to contribute to the policy debate. These highlight the potential of multi-actor coalitions which can develop from specific agroecological initiatives and activate positive dynamics, bringing in multiple interventions of municipalities.