From Kiev to Moscow
Stephen was a native of Kiev and accepted monasticism at the Caves monastery, where he spent several years in deeds of obedience and prayer.
The oppressions of the Latins — Catholic pressure on the Orthodox Christians of Kiev — compelled him to leave and journey to Moscow. There Great Prince Ivan II, who reigned from 1353 to 1359, received him graciously and supported his settlement near Gorodisch, in the locale of Makhra, approximately 35 versts from the Trinity-St. Sergius monastery.
Founding the Makhrishche Monastery
Though Stephen initially preferred solitude, he eventually yielded to the requests of those who wished to live under his guidance. In 1358 he established his first monastery at Makhra, dedicated to the Holy Trinity, and served as its igumen.
When local nobility — the Yurkov brothers — threatened to kill him out of concern over the loss of their land, Stephen relocated northward. Sixty versts north of Vologda, at the River Avnezha, he founded together with his disciple Gregory a second monastery, also in the name of the Holy Trinity. Prince Demetrius provided liturgical items for it, which Stephen redirected to his original monastery at Makhra.
Friendship with St. Sergius of Radonezh
When St. Sergius of Radonezh left his own monastery seeking a place for solitary ascetic labor, St. Stephen received him. He gave Sergius his own disciple Simon, enabling the great ascetic to found a monastery on the river Kirzhach.
Stephen's spiritual approach balanced strictness toward himself with compassion toward others. He took an active part in the labors of the monastery and guided his monks through gentle and quiet conversation. In his final years he became a schemamonk, taking up the strictest monastic schema.
Relics & Shrines
In 1550, during the construction of a new stone church dedicated to the Holy Trinity at Makhrishche, Stephen's relics were found to be incorrupt.
By tradition, his relics were glorified by reports of help in various sicknesses and misfortunes for those who called upon his name.
