Novhorod-Siverskyi first appears in the chronicles in 1044, and by 1098 it was the capital of the Siverian Principality, a frontier realm whose task was to shield the Rus' lands against the Cumans and other peoples of the steppe. That role gave the town its enduring fame through Prince Igor's campaign. Then came a thousand years of changing masters. The Mongols destroyed the town in 1239; afterward it passed to the princes of Bryansk, then to the Grand Dukes of Lithuania, ruled at one point by Dymitr Korybut, a son of Algirdas. Moscow won the area after the Battle of Vedrosha in 1503, lost it to Poland during the Time of Troubles, and regained it in the war of the mid-seventeenth century. In 1620 the Polish king Sigismund III Vasa granted the town Magdeburg rights, making it the easternmost county seat of Poland.

Despite centuries of upheaval, Novhorod-Siverskyi has kept a remarkable stock of architecture, scattered across high river capes divided by ravines. The crown of it all is the Monastery of the Saviour's Transfiguration, once the residence of the Chernihiv metropolitans. Within its seventeenth-century stone walls, and above foundations reaching back to the sixteenth century, rises a cool neoclassical cathedral built between 1791 and 1796 to a design by Giacomo Quarenghi, the Italian architect who shaped so much of imperial St. Petersburg. Elsewhere in town stand the Cossack Baroque Assumption Cathedral, a triumphal arch raised in 1787, and the wooden church of St. Nicholas from 1760, its timber walls a survivor of the region's older vernacular. Streets of eighteenth- and nineteenth-century houses fill in between, giving the old center an unplanned, organic shape.

For a modest city, Novhorod-Siverskyi has sent a striking number of figures into the wider world. The Cossack Baroque poet and archbishop Lazar Baranovych worked here in the seventeenth century; the writer Panteleimon Kulish and the historian Mykhailo Maksymovych were born here; so, improbably, was Zino Davidoff, who would leave to found the Davidoff cigar and cigarette house in the West. The twentieth century brought harder history. The town was occupied by the German Army from 1941 to 1943, and its Jewish community was murdered during the Holocaust, a loss now documented among the untold stories at Yad Vashem. In 2022 the city was again occupied and its people forced to endure a humanitarian crisis before it was retaken. Through every one of these chapters, the monasteries have kept their place on the bluffs above the Desna.