This Paper examines the distribution of megalithic and rock-cut structures, analysing their spatial and temporal characteristics in Samtskhe-Javakheti, Georgia. A new landscape map, compiled by us in 2024, delineates 43 classification units. Information on rock-cut and megalithic structures was sourced from field studies, large-scale topographic maps, and the online portal Memkvdreoba.ge. Thematic classifiers were developed to group landscapes based on the following criteria: (a) Hypsometric levels; (b) Relief forms; (c) Relief types; (d) Ecosystems. The study identified and assessed 77 rock-cut monuments and 218 megalithic structures across administrative and landscape units. Key findings include (I) Rock-Cut Monuments. About 89% are associated with volcanic landscapes. Concentrations are within the middle mountainous belt, particularly in steppe, meadow-steppe, and semi-humid forest-shrub ecosystems. (II) Megalithic Structures. Concentrate on the Javakheti Plateau. Approximately 85% are associated with volcanic relief, with 55% situated in the middle mountains and 43% in the subalpine belt. Their distribution aligns predominantly with steppe ecosystems, especially middle mountain and subalpine steppe zones. This research highlights the interplay of natural and cultural landscapes in Samtskhe-Javakheti, offering a foundation for further exploration of this region’s rich heritage.