The exact time of the founding of the Ryazan Holy Trinity Monastery is unknown, but tradition links it to the visit of St. Sergius of Radonezh to Ryazan, who sought to reconcile Grand Duke Dmitry Donskoy of Moscow and Grand Duke Oleg Ivanovich of Ryazan. According to chronicles, this occurred in 1386, when Ryazan was called Pereyaslavl Ryazansky. In the 16th century, the Ryazan principality was subjected to frequent raids by Tatar-Mongol hordes, which led to the destruction of all fortresses and records of the monastery. The first mention of the monastery after this refers to the end of the 16th century. In the 19th century, the monastery reached its peak. Its architectural dominant was a four-tiered bell tower, visible from afar when approaching Ryazan. It housed eight bells, the largest of which, cast in 1862, weighed 4.24 tons, and the second, a polyelai bell, cast in 1905, weighed 1.1 tons. The monastery was surrounded by a fence 427 meters long with five round towers and two entrances. On the pediment of the northern gate was a fresco depicting St. Sergius blessing the brethren. The southern gates were framed by two two-story buildings: the brotherhood building, constructed in 1855, and the refectory, built in 1903. The transfer of the monastery to the Church began in 1995, and by the decision of the Holy Synod, Hieromonk Andrei Krekhov was appointed as the abbot of the newly established Holy Trinity Monastery. The oldest temple of the monastery, the Holy Trinity Cathedral, was founded in 1685. It is not distinguished by outstanding architecture but is sturdy, considering the loads associated with its use during Soviet times. Services began there in 2000.

The Church of St. Sergius of Radonezh, a unique warm temple, uses felt in its walls. Services have been held there since 1995. The small church in honor of the icon of the Mother of God "Znamenie-Korchemnaya" and the holy princes Peter and Fevronia of Murom is located on the second floor in the Holy Gates, and services began there in October 2000. Among the relics of the monastery is the locally venerated miraculous icon of the Mother of God of Kazan, the only surviving icon from before the persecutions. The monastery houses relics of Ryazan saints, the holy martyr Misael, St. Theodorit, St. Gabriel, St. Meletius, as well as the remains of Ryazan hierarchs: Archbishop Alexius Titov, Archbishop Anthony, Bishop Guriy of Luzhetsk, Bishop Michael, and Metropolitan Stefan of Yavorsky. A piece of the Holy Sepulcher is kept in the carved wooden cross of the monastery. There are also icons of St. Andrew the Apostle and St. Sergius of Radonezh with pieces of their relics. The monastery has two church dependencies: the Church of the Nativity of the Mother of God in the village of Abryutino and the Church of St. John the Theologian in Plakhino. In the village of Yekimovka in the Ryazan district, a monastery farm operates. Important events in the life of the monastery include the opening of the monastery on December 25, 1995, by the decree of the Holy Patriarch and the Holy Synod, the publication of the newspaper "Holy Gates" since June 1998, the creation of a Sunday school in September 1999, the consecration of the Trinity Cathedral on June 16, 2000, by His Eminence Simon, and the stay in Ryazan of the miraculous icon of the Most Holy Theotokos "Kazan-Vyshenskaya" in July 2001, whose procession began from the Holy Trinity Monastery.