The main street of Tver originates in the far Middle Ages, but a relatively clear idea of this “highway” may be traced only starting from the 17th century, when the development and urban planning structure of the Russian city, in accordance with peculiar views of reality, were reflected in the works of icon painters, as well as foreign travelers. The era of Peter I strengthened the documental use when depicting the layout of a late medieval city, yet the fixation of urban planning structure was largely spared from instrumental survey, since domestic cartographers of the first quarter of the 18th century, as a rule, preferred to focus on the iconographic tradition. Residential, religious and other urban objects are represented in these materials in quite a schematic and sometimes generalized way. The situation changed by the middle of the 18th century, but this period (the second quarter — the middle of the 18th century) in the cartographic heritage of Tver still remains a blank spot. For this reason, it is currently quite difficult to outline the route of the city’s main highway in the pre-Catherine era, since in the mid-1760s the direction and configuration of the main street of Tver were changed by the initiative of Catherine II. Nevertheless, this study attempts to reconstruct the location of the pre-Catherine “highway”, as well as to present the nature of almost completely lost urban development associated with this street in the late Middle Ages and in the first half of the 18th century.