This article explores the role of a specific Localised Agri-food System (LAFS) in the provision of Environmental and social benefits (ESBs) in densely cultivated, industrialised, and populated areas by analysing the core of the processing tomato supply chain of northern Italy (Parma and Piacenza). The research examines how the interplay of market drivers, public policies, and collective actions favoured farming, technological, and organisational innovations geared to support long-term economic growth and tackle, at the same time, environmental challenges. The tomato supply chain is characterised by a favourable convergence of attitudes, policies, and market conditions that over time allowed for fruitful interactions between private stakeholders and between the supply chain and public players. Decades of key stakeholders’ interconnections within the tomato supply chain led to a success story of economic growth and attention to a new balance between agro-industry and environment, for the benefit of producers/processors, consumers, and natural resources. Profitability strategies inevitably imply intensification of farming in order to maximise profit levels per hectare, however, the tomato supply chain found a collective motivation that could grant profitability and concurrently reward producers and processors for attention paid to safeguarding the environment—giving evidence that intensification does not necessarily conflict with requirements in support of sustainability.