Situated far to the south in the Pirin area, this is the only monastery restored during the first centuries of Ottoman rule, which has survived to this day. The present-day appearance of this old monastery dates back to the XVI century. According to one inscription, the image of Christ Pantocrator together with the twelve apostles above the entrance gate of the Holy Virgin main church was painted in 1597. Valuable monuments of XVII century painting included the external southern wall (Doomsday, Jacob's Ladder), dated with an inscription from 1611, as well as scenes from the life of John the Baptist painted in 1622 in the ossuary.
The inside walls in the naos, the narthex and chapel of the main church were painted in 1732, with a strong inclination for narration, with more than 150 subject-matters illustrated. The abundance of figures of monks and hermits unknown anywhere else, many of them, probably historic personages, are also typical.
Rozhen Monastery owes its fame above all to its carved iconostases and lecterns. Some of them are extremely complicated compositions, both in intent and in actual execution, in which Biblical themes have given full scope to boundless imagination, which reached the peaks of decorativeness.
Rozhen Monastery has left us with a treasure in yet another art - that of calligraphy. A unique work of the calligraphic school, which existed here as early as the XIV century, is the manuscript "Interpretation of Jonah", taken in 1674 from the Constantinople Patriarch Dositheusm, and kept today in the Holy Grave Church in Jerusalem.
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