According to legend, this place got its name because Bishop Pitirim loved to stroll here. It is said that on September 15, 1688, he, along with Saint Mitrofan of Voronezh and monk Innocent, chose a site for the future monastery in the Tsensky forest near Tambov. The first builder and abbot of the monastery was Hieromonk Varlaam, and the saint had his cell in the monastery. Initially, the monastery was called the Precursor Desert, and from the second quarter of the 18th century, it became a monastery. It was located half a kilometer from the bank of the Tsna, deep in the forest, east of the current site. In 1691, a wooden church dedicated to St. John the Forerunner was built. According to tradition, Pitirim himself dug a well with healing water in the monastery. In 1717, a fire destroyed almost the entire monastery, including the church. The restored church lasted until 1753 when it was dismantled due to dilapidation. A wooden Introduction Church was built in its place, which stood until 1790. Under Bishop Theophilus Raev, construction was actively carried out: in 1789, the cells and refectory were rebuilt, and a new abbot's building was erected. From 1790 to 1808, a stone church of the Nativity of St. John the Forerunner was built, and in 1795, the monastery was surrounded by a stone wall. From August 21, 1822, to October 8, 1824, the archimandrite of the monastery was Philaret of Paradise. The second peak of construction occurred at the end of the 19th and the beginning of the 20th century. In 1895 and 1902, a church of the Savior Not Made by Hands was built in the Russian-Byzantine style. In 1901, the iconostases were updated, and the walls of the Introduction Church were painted. In 1903, the construction of the Precursor Cathedral was completed. The monastery was managed by an abbot who often was also the rector of the Tambov seminary. The number of monks did not exceed 20 by 1917. Before the revolution, the monastery was popular among pilgrims and served as a place for retired hierarchs of the Tambov diocese. The monastery's relics included the icon of the Unburnt Bush, a cross with the relics of St. John the Forerunner, and the miraculous icon of the Mother of God "Quick to Hear," brought from Athos in 1867.

After the revolution, the monastery was closed. It housed places of imprisonment, the churches were desecrated, and the graves of archpastors were lost. In 1920-1921, the monastery became the first Soviet concentration camp for participants in the peasant uprising led by A. S. Antonov, through which more than 27,000 people passed. At the end of 1922, the concentration camp was disbanded. In 1927, the Tambov branch of the correctional labor house was located here, later various military units, and from the early 60s, a military training ground. The surviving buildings, including churches, housed military warehouses. The final destruction of the churches and the entire architectural complex occurred in the 1950s-60s. Only a few structures survived: the refectory, the monks' cell building, stables, an icehouse, and hay dryers.

In 1998, the revival of the monastery began. The slope by the river was cleared, a well was dug, and the construction of a church and a covered bathing area started. In 2002, a new church in honor of the Second Finding of the Relics of Saint Pitirim was built on the territory of the former Trigulyae Monastery, along with a chapel over the spring, which was consecrated on August 8 of the same year by Patriarch Alexy II of Moscow and All Russia. Later, an Archierarchical Courtyard was established. Work on landscaping the territory continues: a fence has been installed, gasification has been carried out, a modern heating system for the church and the abbot's house has been built, and the monastery gates are adorned with the icon of Saint Pitirim. Worship services and pilgrimages to the monastery and the holy spring have resumed. In 2007, the territory of the monastery was transferred from the Ministry of Defense to the Tambov diocese.