The cypress (Cupressus sempervirens) is characterized by a very ancient history linked to the wide employment for the technological properties of its wood and for its symbolic value. Although this tree was often considered as a species introduced in Italy, the first genetic studies showed, instead, the presence of an autochthonous population of C. sempervirens in the forest of Fontegreca (Matese massif, Southern Italy), which constitutes the unique autochthonous cypress woodland present in Southwestern and Western Europe. Therefore, investigations were carried out in selected (using geomorphological criteria) areas of the forest, through soil chemical analysis, identification and 14C dating of soil charcoals. Indeed, we hypothesize that these analyses allow clarifying the history of this woodland characterized by the dominance of the cypress in the forest cover. Areas at medium-low (17–29°) slope gradient on the eastern and southern slopes of the forest were investigated and sampled, following pedological criteria (soil horizons order). Soil morphological and chemical analysis showed humus-rich surface horizons, thin (15–30 cm) and poorly developed (young) soils, overlapping the bedrock limestones. The first soil charcoal analysis data highlighted the presence of a previous landscape characterized by several species (e.g., Pistacia, Ostrya carpinifolia, Juniperus sp. and Pinus sp.) and, probably, by a different forest structure. Ongoing charcoal identification and 14C dating will likely give a better understanding of both (1) the cypress history and (2) the development of this forest landscape.