The monastery is believed to have been founded by a hermit, John of Rila, in the 10th century, during the reign of the Bulgarian Tzar Peter (927-968). St John of Rila, whose relics are exhibited for pilgrims in the main church, in fact lived in a cave about half-an-hour walk away from the present-day monastery complex. The monastery itself is considered to have been built by his scholars, who came to the place to be taught by him.

The monastery has enjoyed great respect and privileges ever since it was established. For instance, all the Bulgarian tzars from Ivan Assen II (1218-1241) to the fall of Bulgaria under Ottoman rule at the time of Ivan Shishman (1371-1393) made generous donations to the monastery. The Donation Deed of Tzar Ivan Shishman (1378) testifies to that and also to the preferences the monastery benefited from. The official support helped the monastery grow into a cultural and religious centre of that time. Indeed it saw its prime in the 12-14th centuries and its upsurge was broken only by the arrival of the Ottomans in the end of the 14th century, which was followed by raids and destruction of the complex in the mid-15th century.

The turn of the 15th century saw the revival of the establishment. This was done with the assistance of the Russian orthodox church, which gave donations to visiting monks in the form of books, money, and church accessories in the second half of the 15th century. The national Renaissance period of the 18th and 19th centuries gave a further impetus to the recovery of the monastery. At that time, the complex was reconstructed and rennovated with donations of wealthy Bulgarians from all over the country (Koprivshtitsa, Teteven, Chirpan, Stara Zagora, Samokov, Sofia).

The present-day look of the monastery dates back to the 19th century. The residential buildings, which form a closed irregular quadrangle, started in 1816. In the middle of the inner courtyard rises the oldest building of the complex - an impressive stone tower, built by the local feudal Sebastocrator Hrelyu in 1334-1335. A small church, which is just a few years younger (1343) stands next to the tower. In more recent times, a belfry was added to the tower (1844). Around that time, the monastery’s main church, “the Nativity of the Virgin” was built as well. The architect is master Pavel Ivanovich, who worked on the building in 1834-1837. The church is a 5-domed one with three altar niches and two side chapels. One of the biggest valuables of the church is its wooden iconostasis with azure fretwork. The wall paintings, finished in 1846, were made by many artists, but it was only the famous Zahari Zograf (whose work can be still seen in quite a few monasteries nowadays) who signed below his works. Besides, the monastery treasures a number of valuable icons painted in the 14th-19th centuries.

The entire complex is quite impressive for its size. The 4-floor residential part consists of no less than 300 monks’ cells, 4 chapels, an abbot’s room, a kitchen, a library and guestrooms for donors. The kitchen is particularly interesting for its really huge cooking vessels. The exterior of the monastery is no less intriguing for its high and severe stone walls (reaching 4 floors and even more at some places) cut through by small windows – reminding of a military fort rather than a monastery.

Once in the complex, it is worth visiting the monastery’s museum, which hosts a unique work of art, namely The Raphael’s Cross. The cross is made of a whole piece of wood (81cm x 43cm) and is named after its creator. The monk used fine chisels, small knives and magnifying lens to carve 104 religious scenes and 650 small figures into the cross. The cross was finished in 1802 after the monk worked on it for no less than 12 years, losing his sight upon completion.

Similarly to other Bulgarian monasteries that survived during Ottoman times, the Rila monastery has acted as a centre of spiritual and cultural life for the Bulgarian nation during the foreign rule. During that time, the monks created new works and made copies of medival Bulgarian authors, representing mainly the Turnovo and Mount Athos schools.

The monastery was declared a national historical monument in 1976, while in 1983 it was inscribed in UNESCO’s list of world heritage.