Abstract. In the early 1980′s, the European chestnut tree (Castanea sativa, Mill.) assumed an important role in the Portuguese economy. Currently, the Trás-os-Montes region (Northeast of Portugal) concentrates the highest chestnuts production in Portugal, representing the major source of income in the region (€50M-€60M). The recognition of the quality of the Portuguese chestnut varieties has increasing the international demand for both industry and consumer-grade segments. As result, chestnut cultivation intensification has been witnessed, in such a way that widely disseminated monoculture practices are currently increasing environmental disaster risks. Depending on the dynamics of the location of interest, monocultures may lead to desertification and soil degradation even if it encompasses multiple causes and a whole range of consequences or impacts. In Trás-os-Montes, despite the strong increase in the cultivation area, phytosanitary problems, such as the chestnut ink disease (Phytophthora cinnamomi) and the chestnut blight (Cryphonectria parasitica), along with other threats, e.g. chestnut gall wasp (Dryocosmus kuriphilus) and nutritional deficiencies, are responsible for a significant decline of chestnut trees, with a real impact on production. The intensification of inappropriate agricultural practices also favours the onset of phytosanitary problems. Moreover, chestnut trees management and monitoring generally rely on in-field time-consuming and laborious observation campaigns. To mitigate the associated risks, it is crucial to establish an effective management and monitoring process to ensure crop cultivation sustainability, preventing at the same time risks of desertification and land degradation. Therefore, this study presents an automatic method that allows to perform chestnut clusters identification, a key-enabling task towards the achievement of important goals such as production estimation and multi-temporal crop evaluation. The proposed methodology consists in the use of Convolutional Neural Networks (CNNs) to classify and segment the chestnut fruits, considering a small dataset acquired based on digital terrestrial camera.