It is believed that Dryanovo Monastery dates back to the Second Bulgarian State. Thus, although it was repeatedly destroyed and rebuilt later, the monastery existed for nine whole centuries. The monastery is situated 5 km. southwest of  Drianovo town, surrounded by the majestic scenery of  Dryanovska River and Andaka River.

Around the 14th century Dryanovo Monastery was ahesychasmos center( also: palamism; a form of constant purposeful prayer or experiential prayer, explicitly referred to as contemplation. It is to focus ones mind on God and pray to God unceasingly;  later on: an Eastern orthodox dogma) and sheltered many monks that practiced the mystical teaching. During the Renaissance, the monastery became a stronghold of Bulgarian spiritual leaders and revolutionaries. In the complex there’s a large library, as during that time it was one of the most important educational centers in the country. Deacon Vasil Levski – The Apostle, Father Matthew Preobrazhenski (Mitkaloto), Georgi Izmirliev and other fighters for freedom have stayed here. During the April Uprising, Pop Hariton and Bacho Kiro’s detachment absconded here as well. After a fierce fight with the numerous Ottoman army, the Bulgarian squad was defeated, the monastery-  burned and ruined  to the ground. Soon after the Liberation,  Dryanovo monastery was built again, and today it is one of the most revered Orthodox shrines and it is declared a national monument.