Since 2015, the ongoing project “Harvesting Memories” has been focused on long-term landscape dynamics in Sicani Mountains (Western Sicily). Archaeological excavations in the case study site of Contrada Castro (Corleone) have investigated a settlement which was mainly occupied during the Early Middle Ages (late 8th–11th century AD). This paper aims to understand the historical suitability and sustainability of this area analysing the correlation between the current dynamics of plant communities and the historical use of woods detected by the archaeobotanical record. An integrated approach between phytosociology and archaeobotany has been applied. The vegetation series of the study area has been used as a model to understand the ecological meaning and spatial distribution of archaeobotanical data on charcoals from the Medieval layers of the Contrada Castro site. The intersection between the frequency data of the archaeobotanical record and the phytosociological analysis have confirmed the maintenance of the same plant communities during the last millennium due to the sustainable exploitation of wood resources. An integrated comparison between the structure and composition of current phytocoenoses with archaeobotanical data allowed us to confirm that this landscape is High Nature Value (HNV) farmland and to interpret the historical vegetation dynamics linked to the activities and economy of a rural community.