On the site of the current church in honor of St. Simeon Stylites, there were originally two wooden churches: a cold one in honor of St. Simeon Stylites and a warm one in honor of St. Basil of Caesarea. The exact dates of their founding are unknown, but the first mentions of them date back to the late 15th century, specifically to 1471, when the first miracle occurred at the tomb of the righteous Procopius of Ustyug. These churches are also mentioned in the 1630 Census Book. According to descriptions from 1676 and 1683, there was a five-domed cold church in honor of St. Simeon Stylites with three chapels and a two-domed warm church in honor of St. Basil the Great, as well as a bell tower with nine bells. In 1715, they were destroyed in a fire. On June 20, 1725, the Archbishop of Veliky Ustyug and Totma, Bogolep, issued a decree for the construction of a stone two-story Simeon church. The first floor was warm, in honor of St. Simeon Stylites with a chapel in honor of the Apostle James the Less, while the second floor, cold, was in honor of the Nativity of the Most Holy Theotokos with chapels in honor of St. Nicholas the Wonderworker and Prince Vladimir. The construction was completed in 1747. In 1757, the church suffered from a fire, and in 1765 it was restored with funds from merchant I. Ya. Kurochkin.

The interior and iconostasis of the Church of St. Simeon Stylites also date back to 1765. The main room of the temple was richly decorated with stucco. The lower floor housed the warm church in honor of St. Simeon Stylites. In the niches of the church were ancient icons adorned with silver and pearls. Among them stood out the icon of the Mother of God of Vladimir with a silver cover decorated with pearls, and the icon of the Sign of the Mother of God with an inscription indicating its correspondence to the miraculous image from Veliky Novgorod, painted in 1715. There was also the icon of the Mother of God of Tikhvin with an inscription confirming its correspondence to the miraculous image painted in 1720, and the image of St. Simeon Stylites with a life story, which comes from the ancient wooden church and is now kept in the State Tretyakov Gallery. The refectory iconostasis was made of wood, painted, with carved and gilded cornices. In total, it contained eleven images, among which was the image of the Almighty with an inscription stating that they were painted by the keymaster Athanasius and his companion in 1752.

In 1765, a separate bell tower was built near the Simeon church. In 1771, Ustyug master Matvey Bushkovsky cast a bell weighing 154 poods for the church. As a result of one of the floods, the porch of the church facing the river was severely damaged, and what has reached us dates back to 1908. The newly finished upper cold church of the Nativity of the Theotokos was consecrated on May 18, 1908. In February 1930, the church was closed, after which the dismantling of the bells and iconostases began.

On May 20, 2001, worship services resumed at the Church of St. Simeon Stylites, and on March 7, 2003, the church was consecrated.