The history of Tikhon Monastery begins in the second half of the 15th century, when a monk from the Moscow Chudov Monastery, Tikhon, came to the Medyn forests. He lived alone for several years in the hollow of an old oak until disciples gathered around him. Eventually, despite the resistance of the local prince Yaroslav Vladimirovich, a monastic community was formed. Like many young monasteries, it was materially poor, having only a wooden Assumption Church and a few cells, but spiritually rich thanks to the teachings of the venerable Tikhon.

In 1551, at the Moscow Council, Venerable Tikhon was canonized. His relics were discovered and rested in the Assumption Church. In 1610, Polish-Lithuanian troops destroyed the monastery, destroying all monastic documents that could have helped restore the history of the first century of the monastery's existence. Only the church in honor of the Three Hierarchs survived. The monks hid the relics of Venerable Tikhon, fearing their desecration.

The restoration of the monastery began a few decades later. By 1630, new economic buildings and cells were constructed, and then the construction of two new wooden churches began. In the 1670s, the construction of a stone church over the relics of Venerable Tikhon of Kaluga began. The Three Hierarchs Church was moved outside the monastery and became a parish church. The stone church was consecrated in honor of the Transfiguration of the Lord.

In 1684, Tikhon Monastery lost its independence and was annexed to the Moscow Don Monastery. The establishment of the Kaluga Diocese in 1799 organized the life of the monasteries. By the end of the 19th century, the monastery experienced a material flourishing: the Transfiguration Cathedral was rebuilt, new churches and a bell tower were constructed. In 1914, a new Assumption Church and a hospital building with a church were consecrated.

By 1917, Tikhon Monastery had become one of the largest monasteries in Russia, second only to Optina Pustyn in the number of pilgrims. However, in 1918, the monastery was closed by the decision of the Kaluga district congress of workers' deputies.

In 1993, the Assumption Cathedral was transferred to the Kaluga Diocese. The first liturgy took place in 1995, and restoration work continued for another five years. Currently, the Assumption Cathedral, Nikolsky Church, house church with the hospital building, brotherly cells, and refectory have been restored. A church has been built at the holy spring, restoration of the bell tower is underway, and new churches are being constructed. Daily services are held at the monastery.