Chestnut stands (orchards and coppices) are among the most typical elements of the southern European mountain landscape and a protected habitat (9260 Castanea sativa woods) according to the European Union (Directive 92/43/EEC). As an anthropogenic landscape, they require specific measures to address preservation or to guide their evolutionary trend. In the Northern Apennines, a landscape multiscalar-multitemporal approach was adopted to highlight factors that have acted on the evolution of this habitat and which still might affect either its preservation or its evolutionary dynamics. Using a diachronic GIS-approach, we analyzed old cadastral maps (drawn up 200 years ago), and aerial photographs. Both the present distribution pattern of the woody species and the incidence of important chestnut diseases were also surveyed. The factors explaining the current extent and species composition of the local chestnut forests confirm their status as an anthropogenic habitat. The present landscape distribution of chestnut woods is heavily linked to past human settlements. Chestnut blight and ink disease are more an indirect reason for past felling activities than an actual direct cause of damage to trees, because of the hypovirulence spread and the limited incidence of the ink disease. Vegetation dynamics of abandoned chestnut forests evolved only partly towards deciduous Beech and Hop Hornbeam stands, thus suggesting both the possibility of a recovery of this cultivation and the need for new criteria for its management.