The monastery was built during the reign of Tsar Ivan Shishman (1371-1393). The legend of Tsar Ivan Shishman's last desperate battles with the Turkish invaders is connected with it. After a bloody battle, the places where the monastery stands today were covered with many skulls (β€žcherepβ€œ in Bulgarian) of fallen warriors, and the entire surrounding area was also scattered with them. From these skulls comes the name of the area "Cherepich" (scull is β€žcherepβ€œ in Bulgarian). There is another area called Shishmanets between the monastery and the village of Lyutibrod. In one of the caves, they say, the wounded king Shishman spent the last days of his life. These caves are called "Shishmanovi dupki" or "Shishmanovi pesheri". His golden treasure is also hidden here.

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    The Church History and Archeology Museum in Sofia preserves a typikon of the monastery, compiled around 1396, which shows that it was destroyed during the battle and rebuilt immediately afterwards. The remains of its medieval church are located under the current one. Therefore, since the 14th century, the monastery has been located in the same place. Nothing is known about the history of the Cherepish monastery over the next two centuries. In his "Slavonic-Bulgarian History" in 1762, Paisii Hilendarski noted that the famous Bulgarian artist Pimen Zografski "renovated the Cherepish monastery by the Iskar River, and died here... in 1610". In the life of "St. Pimen", written by the Cherepish monk Pamfilius, it is noted that after he renovated the monastery, "he gathered many brothers, appointed an abbot for them and arranged everything as in the Zograf monastery". Moreover, even during his lifetime, Pimen Zografski was an initiator of the development of literature, whose masterpiece is the famous "Cherepish Four Gospels". It was written at the end of the 16th century, the size of the book is 31/20 cm, and the covers have a gilded embossed silver binding. The masterful miniatures of the binding depict the biblical scenes of the Crucifixion and Resurrection on the front, and on the back - the Annunciation and the Exaltation of the Holy Cross. The binding was made in 1612 by the Chiprovtsi masters Nikola and Pala. The original manuscript is the work of at least two or three scribes. However, based on the nuances in the graphic appearance of the letters and the way they are written, it is difficult to establish the exact boundary when changing the handwriting. There are two hypotheses about the place where the relic was created. The first is that this happened in the monastery school at the Cherepish monastery, from where the name of the Four Gospels probably comes from. The second is that it was brought from Athon Monastery (Greece) by Pimen Zografski himself to become the non-religion gospel of the Cherepish monastery renovated by him (1612). The luxurious binding is also a sign that the manuscript was commissioned and donated - such a gesture was usually associated with the consecration of a renovated temple. There is also an opposite thesis to this one, and it is based on the similarity in the decoration (mostly with the abundant use of gold) of the Cherepish Gospel and the popular Boychoβ€˜s Gospel, written in 1577 by Boycho Grammatik. It is assumed that for reasons unknown at the moment and by unknown paths, a Slavic Four Gospels (most likely Ukrainian) decorated with miniatures and gold reached the Bulgarian lands and became a model for the writers of the time. The Four Gospels are written on paper (Bulgaria was one of the first countries in Europe to replace parchment with paper - since the time of Ivan Asen II. And all written records have been on paper since the 15th century). Traditionally for the time, black ink was obtained from the fruits of black elderberry and oak sapwood.
    The Four Gospels were kept for a long time in the National History Museum, where they underwent restoration between 2003 and 2010, and since 2010 they have been in the Regional History Museum - Vratsa. Several other literary monuments from the monastery are known - the Gospel of Danail from 1616, the Panegyric from 1623, the Apostle from 1630, the work of the monk Jacob. And the literary activity continued with unabated activity in the following 18th century. Some books written at that time in the monastery are known - the Typikon from 1737, the Anagnost from 1745, the famous "Margaret" by Todor Vrachanski from 1762 and others. At the end of the 18th century, the bandits raids briefly depopulated the Cherepish Monastery. In 1798-1799, Sophrony Vrachanski came here twice to seek refuge, but he did not find anyone, because the monks had hidden themselves and lived in the surrounding caves. According to one of the legends, Sophrony spent several weeks in one of the caves in the rocks opposite the monastery - Toplica. It was not until 1802 that life in the monastery was resumed by priest Tornyo, who renovated the church and built a small residential building north of it. In the first decades of the 19th century, the monastery became wealthy and its abbots received funds to develop a rapid construction activity. By the end of the 19th century, the monastery had already developed into two courtyards - a pilgrimage and a monastic one. The monastery became a significant center, as evidenced by the facts that the Strupec (Tarzhishki) monastery had the status of a nunnery to the Cherepish monastery. In the 17th century, a monastery school was established in the monastery. Later, monastery schools existed not only in the monastery itself, but also in its nunnerys. In the Teteven nunnery, which had existed since before 1840, teacher Yoto Kifalov introduced some of the first educational ranks in the Bulgarian lands.
    The abbot of the Cherepish monastery, hieromonk Epiphanius, was very active and enterprising. He, together with the monks Dionysius, Seraphim, Pachomius, Ionius and Theodosius, participated in the Vratsa conspiracy and were members of the local revolutionary committee. The abbot even being its founder and chairman. It is a proven fact that Vasil Levski and Nikola Obretenov visited the Strupec Monastery, located further down the Iskar River in the area of ​​the village of Strupets, which for years was a nunnery of the Cherepish Monastery..
    In 1889 and 1907, the Cherepish Monastery was also visited by Ivan Vazov and the events of his famous story "A Bulgarian Woman" take place near it. In 1897, the monastery was a stopover for Aleko Konstantinov during his journey through these places, after which his travelogue "Bulgarian Switzerland" was born. Although rebuilt and renovated many times, the Cherepish Monastery has retained its ancient appearance. The monastery is a complex consisting of a church (from the beginning of the 17th century) and buildings built in the 19th century during the time of Abbot Joseph (Vladishka House, Methodius Building, Rashid House, Danail House, Reception Building, school, cemetery park "St. John the Baptist" and chapel "St. Pimen Zografski"). On one of the rocks, right next to the walls of the monastery, the so-called "Rushid House" was built from the beginning of the 19th century. The legend tells that it was built by Rushid Bey, the governor of Vratsa. He had a daughter who was seriously ill with tuberculosis. One night, a Woman appeared to the girl and told her to go to the Cherepish Monastery. The desperate parents immediately took their daughter to the monastery, where they read a prayer for her health and she actually recovered. As a sign of gratitude, the Bey built the building on the inaccessible rocks. According to legend, the fatal decision to rob the Orkhanie post office by a group of revolutionaries led by Dimitar Obshti on August 15, 1872 was made in this house. The church was completely painted three times: in the 17th century, in the second half of the 19th century, and in 1941. The iconostasis dates from the 19th century and is the work of masters from the Tryavna woodcarving school.
    The architectural type of today's monastery church confirms that it was indeed built around the end of the 16th century. The church (18.50 x 7 m) is single-nave. In the 19th century, the narthex that existed until then was united with the nave, and the windows were also expanded at the same time. After this reconstruction, the church was repainted by priest Ioaniky (perhaps the priest Ioaniky Vitanov from Tryavna). It was discovered that parts of the old frescoes, possibly painted by St. Pimen Zografski before 1610, are preserved under these frescoes. The altar tract has a canonically shaped prostheses and diaconicon. In 1908, the iconographer Vasil Iliev from Galichnik, Debar region, painted for free the dome and the space of the former narthex, joined to the nave of the monastery church. The octagonal drum and the dome of the church were erected in 1888. The current narthex dates from 1939, and the exonarthex is from that time. The iconostasis with exquisite woodcarving and a shroud, exported in 1844 is among the sights of the interior decoration of the temple. The hieromonk Epiphanius built a two-story monastery ossuary in the rocks above the monastery courtyard in 1884. Its chapel, dedicated to "St. John the Baptist", was consecrated on August 20, 1888 by the Vratsa bishop Konstantin. The Sofia Theological Seminary "St. Ivan Rilski" was moved next to the Cherepish Monastery after September 9, 1944. It is returned to Sofia after November 10, 1989. A large church - "St. Kliment Ohridski" - operated at the seminary, currently abandoned.
    A railway station was built because of the monastery and the Seminary. Nowadays, the monastery continues to be active and inhabited by monks. The Cherepish Monastery has been declared a cultural monument.


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