unique position of Vologda on important waterways connecting Moscow, Novgorod, and the White Sea (via the Northern Dvina) made it attractive for the Novgorod Republic, as well as for the princes of the Tver and the Moscow, who fought numerous wars between the 13th and the 15th centuries.
In 1371, Dmitry Prilutsky, a monk from the Nikolsky Monastery in Pereslavl-Zalessky, founded Nikolsky Monastery, now known as Spaso-Prilutsky Monastery, close to the city. Dmitry Donskoy, the Grand Prince of Moscow, was the chief benefactor of the monastery and viewed it as a stronghold of the influence of the Grand Duchy of Moscow in the Northern lands in competition with Novgorod.
In 1397, during the reign of Vasily I, Vologda was added to the Grand Duchy of Moscow. Subsequently, the city was several times attacked by Novgorod forces. During the Muscovite Civil War, Vologda played a key role. After Vasily II the Blind, the Grand Prince of Moscow, was defeated by Dmitry Shemyaka in 1447, he swore to never start a war against Shemyaka, was exiled to Vologda, and got the city as a personal possession. From there Vasily traveled to the Kirillo-Belozersky Monastery where the hegumen released him from the oath. The civil war continued, and in 1450, Vologda was besieged by the troops of Dmitry Shemyaka; however, they did not manage to occupy the town.
After the death of Vasily in 1462, Vologda passed to the possession of his son Andrey Menshoy and became the center of the Principality of Vologda. In 1481, after the death of Andrey who had no successors, Vologda passed to Ivan III, the Grand Duke of Moscow, and was included to the Grand Duchy of Moscow.
Times of Ivan the Terrible
During the reign of Tsar Ivan the Terrible, Vologda became one of the major transit centers of Russia's trade. The foreign trade was conducted mostly with England, Holland, and other western countries via the White Sea. Arkhangelsk was the major foreign trade haven, and
