The monastery was founded by Saint
Demetrius of Priluki, formerly a
hegumen of the
Nikolsky Monastery in
Pereslavl-Zalessky. Demetrius (aka Dimitry) left Pereslavl since he thought it was too crowded, and moved north. He first decided to settle down on the
Obnora River (currently in
Gryazovetsky District), but he was not accepted warmly by the local population, so he moved further north. After coming to a meander (
priluka) of the Vologda River, he built a wooden church and the cells. The place came to be known as Priluki afterwards. The
Grand Dukes of Moscow (starting with
Dmitry Donskoy) supported this monastic establishment in order to expand their influence in the
Russian North.
Vasily III of Moscow visited the monastery personally in 1528, when he and his wife
Elena, childless for a long time, had set on a pilgrimage across the Russian North to pray for a child. Their son
Ivan is known to have prayed before
the Cilician ivory cross from the monastery before his
decisive attack on Kazan in 1552. On December 16, 1612, the monastery was captured and burned by Polish-Lithuanian brigands, the so-called
Lisowczycy. As of 1764, it owned more than 100 villages with 2819 male peasants. In August 1924, the Communists had the monastery abolished. The Cilician cross was confiscated, the ancient library and icons dispersed. The buildings were subsequently used for a variety of purposes, including living quarters, a prison, a depot, and a museum. They underwent a comprehensive restoration (starting in 1954) which resulted in a medievalized appearance. In 1991, the monastery was re-established. The relics of St. Demetrius, his staff and penance chains ('''') are still kept at one of the churches. ==Architecture==