The majority of historical urban areas in western countries are paved with stone elements, which have been used since the expansion of land trade routes to the emergence of motorization. Any approach to the conservation and functional and structural rehabilitation of historically significant stone pavements must include an informed preliminary analysis of construction criteria. We present a historical study and engineering analysis of the most common types of stone pavements of this period based on an original database of technical documents, and our focus is on local terminology and constructive methodology used in Italy, Europe, and North America. The authors believe that a historical awareness and knowledge of the types of materials, the functions required of road surfaces, and the reasons for the choices of different soil preparations constitute indispensable requirements for the proper restoration and conservation of this immense common heritage.