Prilep was founded on the ruins of the ancient city of Styberra, first a town in Macedon and later incorporated into the Roman Empire. Styberra, though razed by the Goths in 268, remained partly inhabited.
Prilep is mentioned in 1014 for the first time, as the place where Samoil allegedly had a heart attack upon seeing thousands of his soldiers had been blinded by the Byzantines after the Battle of Kleidion (Kluch). The area of the town and its countryside were one of the most important strategic, political and military places in this part of the Balkans. Many important crossroads, passing from Greece to Adriatic Sea, were crossing through Pelagonia.
It is often called the city under Marko's Towers since the town is located on the skirts of the Towers of the legendary hero King Marko who is common in Macedonian folk songs and tales as apowerful, wise ruler, and fighter against the Turks.
During the period of the Macedonian cultural and national revival, Prilep is very important centre of the Slavic literacy, literature and culture. Educational activities from this period have an extarordinary meaning. They are promoted by the Macedonian teachers Jordan Konstantinov (Dzinot), Dimitar Miladinov, Rajko Zinzifov and Kuzman Sapkarev. Please note the influence of the famous collector of Macedonian folk music, stories, legends and myths, riddles, Marko Cepenkov.
At the period the Ilinden rebellion in 1903, the town was a centre of the Macedonian national movement for freedom. 50 revolutionaries like: Pere Toshev, Gorche Petrov, Petre Acev and many more, were members of the National Liberation Army and what is more important they came from Prilep.
It was here and in Kumanovo, when on October 11th 1941, the struggle of the Macedonian people against fascism begun, during the Second World War. The Tomb of the Unconquered, a memorial in honor of the victims of fascism is placed in the town's spacious and beautiful park.