According to the legend, the Nikitsky Monastery, the oldest monastery in Pereslavl-Zalesky, was founded in 1010. However, the more realistic time of its foundation is 12 century. The monastery is on the north-east bank of Lake Pleshcheevo near the Kleshchinsky complex, the gorodishche (site of ancient town) of the Finno-Ugrian tribe of Merya. 

The first records of Kleshchin date back to 10-11 centuries. Prince Yuri the Long-Armed moved the town to the mouth of the river Trubezh on the south bank of Lake Pleshcheevo in the 12 century. And it was about that time that the construction of the Nikitsky Monastery was begun near the old gorodishche. 

The first years of the monastery are closely related with the life of Nikita the Stylite. The exact date of his birth is unknown and he died in 1186. Already during his life St. Nikita was believed to be a miracle worker and many people came to the monastery for healing. 

Near the monastery is a chapel erected on the place of the miraculous recovery of Chernigov prince Mikhail. No one could cure him of his illness. And when he knew about St. Nikita the Stylite, he came to him and stopped within a verst (about a kilometers) of the monastery. Mikhail sent one of his  boyars  to St. Nikita to ask him for  a remedy of his illness. St. Nikita gave them a staff for Mikhail. And when Mikhail took the staff he immediately recovered. Mikhail had the  cross  installed on the place of his miraculous recovery. The following date was inscribed on it: «the year 6694» (1186). Later, in 1702, a chapel was built on that place.

Before the 16 century all buildings were wooden at the Nikitsky Monastery. A single-domed stone church was built there only under Prince Vasily III in 1528. During 1561-1564, in the reign of Ivan the Terrible, St. Nikita Cathedral appeared at the monastery. The relics of St. Nikita are kept just at this cathedral. In 1668 there were built the bell tower with a tented roof, the Annunciation church and the refectory where Peter the Great stayed during his visits to Pereslavl.