The paper provides a comprehensive architectural and historic-geographical analysis of the monuments of the historic-archaeological reserve, which is world-famous as Old Orhey. This toponym was first found in documents from the end of the 16th century, while the settlement on the Peshtere Cape, where scientists localized it, dates back archaeologically to the 13–14th centuries. Numerous documents attest to the name of the town of Peshtere, which is undoubtedly localized in this place. To resolve the indicated contradictions, determine the reliable localization of geographical names mentioned in historical documents and construct a holistic reconstruction of the geoarchaeological and historic-cultural evolution of the area, the toponymical, historic-cartographical and historic-architectural analyzes of information and objects associated with such an important monument of natural and cultural heritage were carried out. Despite the long-standing debates regarding the cultural interpretation of the artifacts, which remained beyond the scope of this article, the indisputable arguments for their identification are geographical, toponymical and architectural studies, the continuation of which provides a means to get closer to solving the numerous scientific mysteries of this location and the North-Western Black Sea region as a whole.