The article deals with the origin and history of stone construction in Vologda in the 16th century, especially in the last third of the century, when the St. Sophia Cathedral, the fortress and, judging by some information, several stone structures inside the fortress were built. Simultaneity and compactness of the construction allows us to assume the participation of one large brigade. Researchers drew attention to the participation of foreigners Razmysl and H. Locke in the building of the Vologda fortress. But the volumes of construction directly indicate the multiplicity of its participants. In the act of the Trinity-St. Sergius Monastery of January 13, 1586 the Vologda mason Leonty (Pozdey) Vasilyev’s son is noted, who sold the yard to the largest Russian monastery according to this document. Finding the mason in Vologda allows us to assume with a high degree of probability his participation in the sovereign city construction of the last third of the XVI century. The fact that his neighbors sold another part of the courtyard to the Trinity-Sergius Monastery in 1584 leaves no doubt about his acquaintance with the authorities of the Trinity-Sergius Monastery already at that time. Taking into account that in 1585 in this monastery the construction of the largest monastery building at that time - the Dormition Cathedral - was being completed, one can have no doubt that around the time of the transaction with the Vologda mason, the most important Russian monastery needed such specialists. This gives grounds for assumption about the work of the Vologda mason Leonty (Pozdey) Vasilyev’s son not only on sites in Vologda, but also in the Trinity-St. Sergius Monastery. Our assumption can be supported by architectural proximity of the Sofia Cathedral in Vologda and the Assumption Cathedral in the Trinity-Sergius Monastery, oriented on the main Russian temple - the Assumption Cathedral of the Moscow Kremlin. We take into account the interest of Tsars Ivan the Terrible and his son Fyodor Ivanovich in both the Vologda cathedral and the cathedral of the Trinity-St. Sergius Monastery, their location in the same direction from Moscow, as well as the perception of both monumental buildings as typologically similar not only in our days, but already at the end of the XVII century, a century after their building. Attention is drawn to the fact that the yard of the Vologda mason Leonty (Pozdey) Vasilyev's son was white, i.e. free from sovereign taxes, which was usual for the yards of sovereign craftsmen, which is symptomatic, since stone architecture in Vologda and in the Trinity-St. Sergius Monastery in the second half of the 16th century, which took place under vigilant sovereign control, was obviously carried out primarily by sovereign specialists.