Putyvl was first mention as early as 1146 as an important fortress contested between Chernihiv and Novhorod-Siversky principalities of Kievan Rus. The song of Yaroslavna on the walls of Putyvl is the emotional culmination of The Tale of Igor's Campaign and Alexander Borodin's opera Prince Igor.
After the Battle of Vedrosha in 1500, Putyvl was ceded to Muscovite Russia. During the Time of Troubles, Putyvl became the center of Ivan Bolotnikov's uprising and briefly a base for the False Dmitry I forces.
During the Second World War Soviet partisans led by Sydir Kovpak started their guerrilla war against the Germans in the forests near Putyvl. Currently about 20,000 people live in Putyvl. Among the town's architectural attractions the most remarkable are the sixteenth-century Molchansky monastery and seventeenth-century Saviour Cathedral.