According to legend, the monastery was founded at the end of the 10th century by Saint John of Rila (876-946). Saint John lived in a cave near the current monastery, while the monastery itself was built by his disciples who came to the mountains to continue their studies.

In the 14th century, after an earthquake, the monastery was thoroughly rebuilt by the local feudal lord Hrelyo Dragovol, turning it into a solidly fortified architectural ensemble. But in the middle of the 15th century, the Turks plundered and destroyed it. Only the tower (1334-1335), named after Dragovol, has survived to this day.

The monastery's Katholikon (Main Church) was built in the mid-19th century (architect Pavel Yoanov) on the site of a small church from 1343. The church is crowned with 5 domes, has three altars and two side chapels.