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The monastery was founded in 1272 by the Bulgarian ruler Constantine Assen-Tih by the wild waters of the river Vesselina in the foot of the beautiful Balkan Mountain near Elena. This is written in the inscription on the altar apse of the church built in 1835. It is one of the large and beautiful monasteries, a remarkable monument of Old Bulgarian architecture and art.

It was destroyed in the 14th c during the Ottoman oppression. It is believed that it was restored in the 16th c but we lack concrete facts about its activity in the following period. Among the earliest proofs of the existence of the monastery is the so called "Kapinovo beedroll" - a triptych of 1700.

The basic reconstruction of the Kapinovo monastery was made in 1835 when the present church "St. Nicholas" was constructed by the masters Pencho and Racho of Dryanovo. It has a single-nave naos and is covered with a semi-cylindrical arch without domes. In it in 1845 the artist Ivan Popovich painted one of the largest compositions of Bulgarian cult painting depicting the Doomsday. The church preserves many valuable icons from 18th-19th c made by talented masters.

On the east the monastery is surrounded by massive two-storey buildings with stone foundations. They were built in 1866 with funds donated by the Horozov brothers from the town of Elena.

From the outside the monastery looks like a fortress. Inside, the buildings form a wide semicircle and with their wooden stairways, balconies and eves it creates an atmosphere of coziness and peace. The external wall above the central entrance is decorated with mural paintings in which one can see the images of the holy brothers Cyril and Methodius.

On the second floor is the chapel "Presentation of the Blessed Virgin" entirely covered with mural paintings in bright colours. Above the door are depicted the church donors the Horozov brothers and the buildings constructed by them. It is one of the most interesting portraits of church donors in Bulgarian painting of the National Revival.

During the Revival the monastery was an educational centre and in 1830 a school for priests and teachers was opened there.

The monks of the monastery did not stay aloof from the revolutionary activity in the Turnovo region. They offered refuge and support to many participants in the struggle for the liberation of Bulgaria from Turkish yoke.

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