Initially it was founded by Saint Anthony of Pechersk in the 11th century, but ruined in 1239 during the Mongol invasion.
The Trinity Monastery was reconstructed by the famed Ukrainian architect Lazar Baranovych in 1649. In the neighbouring city of Novhorod-Siverskyi, Baranovych founded a printing press, which were rare at the time. He later transferred the printing press to the Trinity Monastery. The monastery's adjacent printing press was famed for their production of engravings, and its library — for containing more than 11,000 books.