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The monastery is situated on the banks of the Cherni Osam near Oreshak, a village 10 km from Troyan in Lovech Province, and is a popular tourist destination.

The first traces of religious life in the area date back to the end of the 16th century, or according to some – to an even earlier time around the end of the second Bulgarian state (turn of the 14th century), when the very town of Troyan was founded. According to the monastery’s chronicles, kept by an unknown monk, the monastery was founded by a hermit who came to the place and built himself a simple cottage some years after the fall of the second Bulgarian state. The monk quickly won the respect of the local people who started visiting him for prayer and advice.

The main church of the monastery was reconstructed near the end of Ottoman rule during the Bulgarian National Revival period by a master-builder called Konstantin in 1835. The ornate interior and exterior of the church were painted between 1847 and 1849 by Zahari Zograph, a popular Bulgarian painter of the time, who also painted the central church of the Rila Monastery, the largest monastery in Bulgaria. One highly controversial move by Zograph was to paint his image around one of the windows in the back of the church.

The iconostasis in the central church is a wood carving dating to 1839.

The Troyan Monastery is also, since the 17th century, the home of one of the holiest icons in Bulgarian Orthodoxy, the Three-Handed Virgin.

Many people make a pilgrimage to this monastery on St. George's Day because of an icon of St. George in the main church.

The monastery’s buildings have a vast hotel part with modernly equipped rooms while there are a few pubs and snack stalls all over the place. One can taste here the famous plum brandy made according to ancient recipes at the monastery itself.