Historic agricultural practices have played a dominant role in shaping landscapes, creating a heritage which must be understood and conserved from the perspective of sustainable development. Agroforestry (i.e., the practice of combining trees with agriculture or livestock) has existed since ancient times in European countries, and it has been recognised as one of the most resilient and multifunctional cultural landscapes, providing a wide range of economic, sociocultural, and environmental benefits. This research explores aspects of the history, physical characteristics, decline, and current state of conservation of historic agroforestry systems on the Northern Apennines in Italy, using an interdisciplinary approach combining archival sources, landscape archaeology, dendrochronology, and GIS analysis. Furthermore, through computer-based modelling, this research aims to evaluate how the abandonment of this historic rural land-use strategy impacted slope geomorphic processes over the long term. The importance of environmental values attached to traditional rural landscapes has received much attention even beyond the heritage sector, justifying the definition of transdisciplinary approaches necessary to ensure the holistic management of landscapes. Through the integration of the Unit Stream Power-Based Erosion Deposition (USPED) equation with landscape archaeological data, the paper shows how restoring the historic agroforestry landscape could significantly mitigate soil mass movements in the area. Thus, the interdisciplinary workflow proposed in this study enables a deep understanding of both the historical evolution of agroforestry systems and its resulting effects for cumulative soil erosion and deposition in the face of climate change.