In existence as early as the Second Bulgarian Kingdom, it was - destroyed and re-built on two occasions. It was restored in its present location - the Dryanovo River gorge, 4 km away from the town of Dryanovo - in 1845. During the 1876 April Uprising, an armed detachment of 200 men, pursued by the enemy, found shelter behind the walls of Dryanovo Monastery. For nine days, they lead a fierce battle before they were finally crushed. The insurgents and monks were killed and the monastery - burned down.
Relics of the April epopee are preserved in the monastery museum today, along with some valuable icons.
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