The article examines a little-studied problem in the period of formation of the system of overland roads in the central part of the Russian state. The purpose of the study is to find out how stable were the road routes in the southern (Zaretskaya) part of the Moscow uyezd in the 17th and the fi rst third of the 18th century. This choice is explained by the fact that the roads in the southern part of the uyezd, separated from its northern (Zamoskovnaya) part by the Moskva river, were a unified complex of communications. The research was based on the cadasters of 1627–1629, Moscow uyezd’s maps of the second half of the 17th century, as well as land surveyor’s plans in the 1720s from the map collection of J.-N. Delisle. The study included identifi cation of settlements indicated on the early 18th-century maps and plans of the second half of the 17th century, a comparison of identified settlements, and search for settlements from the cadasters of 1627–1629 on the basis of comparisons of maps and plans (in some cases, the settlements in the cadasters have references to roads that serve as landmarks). The author concludes that five major roads in southern Moscow suburbs, New Mozhaisk, Zvenigorod, Borovsk, Kashira and Kamensk roads, were formed up to the mid-17th century and kept their importance throughout the 18th century. They were postal highways, “federal highways” of that time. It is impossible to draw a conclusion about the route stability of country roads on the basis of the analyzed sources. The data of cadasters of 1627–1629 allows to confi rm that at least three out of five roads (Borovsk, Kamensk and Kashira) existed not only in the second, but also in the first half of the 17th century. The absence of the Zvenigorod road in the Zaretskaya part of the uyezd in the cadasters does not mean that it did not exist in the first third of the17th century. Most likely the scribe simply did not indicate it as a landmark.