In the 14th century, it was owned by Vladimir the Bold, but passed to the Grand Duchy of Moscow when his granddaughter Maria of Borovsk married Vasily II.

Its strong walls, towers, and a massive cathedral survive from the reign of Boris Godunov.

Two famous Old Believers—archpriest Avvakum Petrovich and boyarynya Feodosiya Morozova—were incarcerated at this monastery in the second half of the 17th century.

[4] Among the monuments of Borovsk are the oldest wooden church in the region (the 17th century) and a museum of Konstantin Tsiolkovsky, who lived and worked there as a teacher in 1880–1891.

Borovsk has recently been known for painted façades of its down-town buildings, resulting from a work of one local painter.