Kumanovo Summer Jazz Festival - This is one of the noteworthy events in Kumanovo held in the period of July and August, which features bands from all over the world.
Days of Comedy Festival - October is the month when the International Theatrical Festival is held, in duration of 15 days. It features comedies from several Macedonian theatres and also from neighbouring countries.
Kumanovo STREETS Festival – open-air multicultural international music festival held in Kumanovo’s main square celebrating the event with local bands, music and dance.
The Art Colony Kumanovo – This art colony is listed among the oldest artistic events. It was established in 1974 between the towns of Kumanovo and Vranje and is held in the art gallery within the City Museum.
The Art Colony Karpino – In the month of July and August, the Multimedia Center Karpino organizes the Art Colony located in the complex of the church in Karpino, 28 km away from Kumanovo.