The area boasts many pre-modern settlements; the oldest are: the Kostoperska karpa, the Bronze Age Gradiste (near the village of Pelince), the Neolithic site of Mlado Nagorichane, the Iron Age tumulus cemetery (village of Vojnik), the Roman Necropolis Drezga (village of Lopate), the Roman Settlement Vicianus (village of Klecovce), and many others.
The city of Kumanovo was first mentioned in 1519 in a document housed in a Turkish archive in Istanbul. The most comprehensive and relevant information on Kumanovo is provided by Evlija Celebija in 1660:
"The colony of Kumanovo is situated on the territory of the Skopje sanjak and represents one county. The city is embellished with many rivers and 600 tile-roofs houses. The mosque in the downtown is beautiful, there are teke, madrassa (Islamic religious secondary school), caravanserai(Turkish bath), a number of shops and water mills; and the climate is pleasant and agreeable. There are many vineyards and gardens."
Kumanovo became an urban settlement and administrative center of the region at the end of the 16th century or the beginning of the 17th century. Following the turbulent events (the Karpos rebellion in 1689) the city experienced a period of stagnation, and by the end of 18th century Kumanovo epitomized an Ottoman provincial town.
A great rebel leader named Karpos was born in a village near Kumanovo called Vojnik. Initially, he was a vassal of Turks, but when the Ottoman empire began to weaken in 1689 and discontent rose concerning new higher taxation policies, Karpos became a turning point in the battle versus the Turks. In that period Austria staged an attack on the Ottoman Empire. Then the Karpos seized upon the situation and the uprising quickly spread to the rebels freeing Kratovo, Kriva Palanka, Kumanovo, Kacanik and in other towns. Then, together with the Austrian army, lead by Emperor Leopold 1st, they fought to liberate Skopje and Shtip.
Later there was a change in the military and political situation in the Balkans, which had a crucial effect on the rebellion. The Austrian army was forced to withdraw and powerful Turkish forces, reinforced by Tatar detachments belonging to the Crimean Khan Selim Giral, attacked the rebels. After fierce battles the Turks took Kriva Palanka, the rebel stronghold, and then attacked Kumanovo and its newly-constructed fortress. Karpos was captured, removed to Skopje, and put to death on the Stone Bridge across the Vardar.
It developed economically in the late 19th century (agriculture, handcrafts and trade). Still, industrial development occurred only at the end of the Second World War. The rapid economic, administrative and cultural expansion of Kumanovo began in 1945. Today, it is a modern city with approximately 70,000 inhabitants.
The anti-fascist insurrection of Macedonians and the struggle for national and social liberation began in Kumanovo and Prilep on October 11th, 1941.