The historical center of Vyazma is considered to be the high left bank of the river, known as "Cathedral Hill," where for centuries the central temple of the city, the Trinity Cathedral, has stood. On the site of an ancient settlement from the 11th-13th centuries, a stone temple was built in the second half of the 17th century. Historian I. P. Vinogradov wrote: "Cathedral Hill is the 'upper small town,' where three wooden towers stood. In the main fortress, between two large towers, the foundation of the new stone cathedral was laid." The first mention of the wooden temple of St. Nicholas at this site dates back to 1015 and is associated with the "Life of St. Arcadius of Vyazma and Novotorzhsk."

According to legends, by the end of the 10th and the beginning of the 11th century, there was a temple on Cathedral Hill in honor of St. Nicholas. During the existence of the Vyazma principality from 1239 to 1403, it was a cathedral. In 1406, Prince Simeon of Vyazma was buried here, having been killed in Torzhok along with his wife Juliana by Prince Yuri of Smolensk. In 1495, the bride of the Grand Duke of Lithuania Alexander, Elena, daughter of Grand Duke of Moscow Ivan III, prayed in the temple. After the capture of Smolensk in 1514, Grand Duke Vasily III prayed in the temple. In 1565, Tsar Ivan IV left a synodic here with the names of those executed during his reign.

By the order of Boris Godunov, in 1597-1598, the dilapidated Nicholas Cathedral was dismantled, and a new one was built in its place with attached chapels of Sergius, the Three Saints, and the Nativity. In 1610, the temple was ravaged by Polish troops under the command of Zholkevsky. In 1612, an appeal from the Sergiev Monastery was read in the cathedral, and a militia was sent to Moscow. In 1635, by the decree of Tsar Mikhail Fyodorovich, the cathedral was rebuilt and renamed the Trinity in honor of the Polyanov peace.

Tsar Alexei Mikhailovich and Patriarch Nikon visited the cathedral in 1654. In memory of this event, a stone cathedral was built with the tsar's funds in 1674-1676. From 1681, by the decree of Tsar Feodor Alexeyevich, a bishopric of Vyazma was established at the temple. In the 17th-18th centuries, the residence of the Metropolitan of Krutitsy stood next to the cathedral.

In 1765, the merchant brothers Kalashnikovs brought a copy of the Iberian Icon of the Mother of God from Moscow to the cathedral. In 1771, when the plague swept through Russia, it miraculously bypassed Vyazma. In memory of this event, a chapel in honor of the Iberian Icon was built in 1773 at the expense of merchant Avksenty Fatov.

During the Patriotic War of 1812, the cathedral was burned and partially destroyed. The French set up a salt warehouse in the surviving part. After the enemy was expelled, the cathedral stood without services for several years. With the funds of the Holy Synod, the cathedral was restored in 1813-1815. At that time, the rector was Archpriest Stefan Goransky.

In 1836, a stone chapel was built from the bricks of the collapsed bell tower near the Smolensk bridge, which existed until the 1930s. In 1847-1849, at the expense of merchant Pyotr Sabelnikov, the Iberian chapel was rebuilt, and a small chapel in honor of Princes Boris and Gleb was added. In 1850, a four-tiered stone bell tower was built. In 1896, after inspections by architect Gunst and engineers Morozov and Yastrebov, work was carried out to strengthen the temple's foundation.

In 1918, the Vyazma vicarage was established. In 1922, silver vestments, utensils, and pearls were confiscated from the cathedral. The cathedral was closed in 1929, and its treasures disappeared. Services resumed at the end of 1941 and have not been interrupted since. Restoration work was carried out in 1974, 1977, 1982, and 2000.

In the Iberian chapel, there is a carved image of St. Nicholas "Nicholas of Mozhaisk," restored in the 1990s. On May 3, 1993, Patriarch Alexy II visited the cathedral. Thanks to the efforts of local benefactors, a chapel was built in honor of St. Arcadius of Vyazma, where a stone on which the saint prayed was placed. A stone arch with gates was built from the side of Lenin Street.