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. Later on, he built a church consecrated to the Holy Virgin.
Between the time of its establishment and 1830, the monastery lived through difficult times, when it was often raided and destroyed, while its monks – killed. The monastery’s dependence on the Greek bishops of the Lovech eparchy, who used its lands and forests for their own enrichment, added to the monastery’s troubles. The solution to the latter problem came in 1830, when a delegation of monks visited the Patriarchy in Constantinople (present-day Istanbul) to present a request for religious, administrative and economic independence of the Troyan monastery. With the help of a supportive letter by the metropolitan bishop of Troyan, Ilarion, the monks achieved what they went to Constantinople for. A special Charter, dated December 4, 1830 and signed by the ecumenical Patriarch Constandios, gave the monastery the desired autonomy, by declaring it “stauropegial” – meaning that it was exempted from the jurisdiction of the local bishop of Lovech and was directly subjected to the Patriarchate of Constantinople. From that point onward, the monastery has expanded and developed into a cultural and religious centre.
The monastery is built in the style of the Bulgarian Renaissance. The chapel of St Nikolay the Miracle-Worker is the oldest but best preserved religious building in the area, though it lies outside the present-day monastery complex, at about half an hour walk south of it. The monastery’s church, “Assumption of Virgin Mary”, was built in 1835 by a master from the village of Peshtera, named Konstantin. The church was built of porous limestone and large bricks in alternating layers, and impressed foreign visitors with its architecture. One such traveller, the Hungarian Felix Kanitz, expressed his admiration at the church in his book “Danubian Bulgaria and the Balkans” in 1871.
Though its parts were built by various masters at different times, the monastery is remarkable for its harmony. The monastery’s dwellings are 3 and 4-storeyed, with long open verandas looking to the inner yard and columns and parapets in the style of old Bulgarian cell-schools. The frescoes of the monastery and the church were painted in 1847-1849 by the famous Bulgarian artist, Zahari Zograf from the Samokov school of art and iconography. The icons of the church represent in their majority works by other masters of the Samokov school, including Zahari’s brother, Dimitar Zograf. Bearing in mind that Zahari and his schoolmates painted a large number of the frescoes at still-preserved monasteries, those at the Troyan monastery remind of many other places, including the popular Rila monastery. Nevertheless, the ornamentation of the Troyan monastery is more lavish with more Baroque branches with leaves and blossoms.
Similarly to the other monasteries at which he was employed (e.g. Bachkovo monastery), here again Zahari painted his own portrait side by side with the portrait of the abbot. Another noteworthy portrait is the group one at the altar, depicting all the 27 monks that lived in the monastery at that time. An interesting painting, which in fact does not fit in the cannons of monastery frescoes, is the one on an outer wall of the living buildings. Zahari Zograf depicted a lion and an elephant, which were to symbolise Bulgarian strength and patience, respectively, during the long Ottoman rule. The woodcarved iconostasis of the church, made entirely of walnut by masters from the Tryavna school of Art, is also impressive.
Similarly to other Bulgarian monasteries, this one also has its miraculous icon, which arrived at the monastery at the time of its establishment, namely the icon of the Three-handed Holy Virgin. According to the story, the icon was donated by a monk who on his way from Mt Athos to present-day Romania learnt about the hermit who lived close to Troyan and dropped by to spend some time with him.
Besides its religious role, the monastery great Bulgarian writers, teachers and translators, including historians such as the monk Spirodon, author of the second book on the Bulgarian history (1792).It was also linked to the Bulgarians’ struggle against the Ottoman rule. Similarly to other monasteries, the Troyan one also hosted frequently the famous Bulgarian Apostle of Freedom, Vassil Levski. The latter formed revolutionary committees not only in the town of Troyan, but also at the monastery itself. The monastery’s secret committee numbered about 80 monks and was headed by archimandrite Makari. During that time (mid-19th century), the production of books at the monastery declined, but this was only at the expense of the monks’ preoccupation with the procurement of arms. During the Liberation Russian-Turkish war, Makari transformed the monastery into a field hospital for Russian soldiers and provided the Russians with all possible assistance.