The convent was founded in the second half of the 16th century. According to the manuscripts of 1628, after it was destroyed by Lithuanian troops, two wooden churches remained in the convent: The Church of Nativity of the Blessed Virgin and the Church of the Prophet Elijah. When tsar Alexei Mikhailovich married a noble woman fr om the Miloslavskie line in 1648, the destiny of the poor convent changed dramatically.
The ancestral lands of the Miloslavskie had been here, in Bolokhovskiy county, and the convent was wh ere their ancestors were buried. Generous gifts were showered on the convent, enabling it to be reconstructed in stone. In 1668, construction began on the first stone building in Orlovshchina, the Troitsky Cathedral. The convent was renamed Troitskaya in its honor. After Maria Miloslavskaya, the biggest contributor, died in 1669, the construction work was stalled until 1706. Other prominent figures donated money to the convent: tsars Fedor Alexeevich, Ioann V, Peter I, the regent Sofia, and the empress Elizabeth I. In 1705, Peter the Great visited the convent and ordered that it be turned into a male monastery. In 1792, the Tikhvinskaya Fair was arranged in the monastery.
In the 19th century, the convent continued to expand. The summer church of St. John the Baptist with a bell tower was built (1861-1864), as well as a new fence with towers, an abbot house, and a house with monk cells. In 1852-1856 the monumental Russian-style Tikhvinskiy Cathedral was erected. The miraculous icon of the Mother of God of Tikhvin became its signature relic. It attracted thousands of pilgrims to the monastery.
The monastery was shut down in 1923, and the Tikhvinskiy cathedral and the church of St. John the Baptist were demolished. The buildings of the monastery were pulled down to make chippings for roads. Only the Troitsky cathedral remained standing.
After the archbishop Paisiy Orlovskiy i Livenskiy blessed it on July 17, 2002, the monastery was reconstituted as a female convent.