The “Harvesting Memories” project aims to address diachronic change in landscape and settlement patterns during the long-term in the area of Sicani Mountains in Central-West Sicily (Italy). This area is a sort of palimpsest of Mediterranean inland areas characterized by a long-term occupation of low-lying lands suitable for agriculture and hills for pastoral activities. The fieldwork survey confirmed this intensity of human presence across the time with site dating back to Middle Copper Age/Eneolithic, Bronze Age, Classical period, Middle Ages and Late Modern age. The dynamics of population of this inner area are well documented in the archaeological sequence of the hill-top site of Contrada Castro. Recent excavation (spring 2017) showed dry-stone structures related to Islamic and Norman period (9th-12th c. AD), a Byzantine infant burial (7th-8th c. AD) and evidence (layer of morphology regularization and pottery) connected to an Archaic indigenous settlement (6th-5th c. BC). The investigation of this new rural site research provided relevant insights of longue durée patterns in hilltop settlements of Sicily between Antiquity and Middle Ages.