Kumanovo is a city in North Macedonia and the seat of Kumanovo Municipality, the largest municipality in the country. Kumanovo lies 340 metres above sea level and is surrounded by the Karadag part of Skopska Crna Gora mountain on its western side, Gradištanska mountain on its southern side, and Mangovica and German mountain on the Eastern side. Skopje airport also serves Kumanovo.

The town was first mentioned in 17th century. It was initially settled by Turks and later by Muslim Albanians. Slavic people entered the town in the late 18th century and early 19th century. It has many historical sites. One of the most important sites is the 4,000-year-old megalithic astronomical observatory of Kokino, located 30 km northeast of Kumanovo and discovered in 2001. It is ranked fourth on the list of old observatories by NASA.

In 1912, during the First Balkan War, Serbian forces won a decisive victory over the Ottomans north of the town. The two-day Battle of Kumanovo ended Ottoman authority in Vardar Macedonia which contributed to the region's integration into Serbia, and consequently, into Yugoslavia.

The rapid economic, administrative and cultural expansion of Kumanovo began in 1945. The town's metal-processing, tobacco, agriculture, footwear and textile industries have made it an economic, trading and cultural center of approximately 135,529 people. It is internationally known for a jazz festival hosting bands from all over the world.