The monastery’s establishment dates back to 1345, the time of the Second Bulgarian State and the reign of the Bulgarian King Ivan Alexander (1331-1371). Fortunately, Virgin Mary of Vitosha was saved from destruction by the Ottoman conquerors. Nevertheless, a few years later, it was abandoned by its monks. Radoslav Mavar, a Sofia boyar, was the man, who renovated and brought back to life the cloister. The beautiful frescoes in the small church of the monastery appeared at the time of reconstruction. The portraits of Radoslav Mavar, his wife and two sons carry the highest artistic value. In the 17th century, the central part of the church was decorated with new wall paintings. In 1932, a new wing was attached to the church. Today the both represent an integral whole with signs of different architectural styles.
Except for the incredible frescoes from different periods, the monastery is famous for hosting a so-called cell school during the Ottoman rule and producing the Dragalevtsi Testament. The monastery took active part in the national revolutionary activity against Turkish domination. The abbot of the monastery, Gennady, helped the national hero Vassil Levski in establishing revolutionary committees in the Sofia region. Vassil Levski hid more than once in the monastery while traveling in the country. After one of the most active members of the revolutionary organisation, Dimitar Obshti, was arrested while the Turkish authorities became aware of Gennady’s underground activities, Father Gennady escaped to Serbia in order to joint another revolutionary, Panayot Hitov. Gennady’s escape however did not put an end to the monastery’s involvement in the preparations for a national uprising, as his successor at the monastery, Father Ignatii of Rila, restored the secret revolutionary committee of Sofia and followed in the steps of Gennady.
One can reach the monastery by car for about 20-30 minutes from the Sofia downtown following a good, asphalt road starting from the centre of Dragalevtsi. Unfortunately, signs showing the way to the monastery are missing, so it is advisable to ask local people from the village of Dragalevtsi for the exact direction. Alternatively, one can take the city bus to Dragalevtsi and then take about half-an-hour walk from the village down shortcut mountain paths – again, it is recommended to check the direction with fellow walkers.