Intercropping landscapes characterised by the presence of certain plant features are usually considered traditional landscapes, important for their biocultural heritage. In recent decades, olive agroforestry systems previously widespread throughout Sicily have transitioned to monocultures alongside the disappearance of other tree species. To analyse the dynamics of land use, we combine mathematical representations and oral narratives of spatial change, focussing our case study on a rural area of inner Sicily, Cozzo del Lampo, characterised by a high presence of century-old olive trees. By using local geonarratives in combination with the results of change detection analysis using historical aerial images spanning 50 years (1955 - 2005), we gain insights into the relationality of people and places over time, highlighting how biocultural heritage is correlated to both local culture and ecology, and demonstrating the value of ecological perspectives to understand past and current human actions. The active engagement of the local population in the interpretation of their own (past-present) practices is key to access new ecological knowledge.