Starting from 1989 year, every October , the largest festival of entertainment music in Macedonia is held in Shtip, "Makfest". The festival produced over 1000 compositions, most of which are hits, and now evergreens.

Many singers had their star moments at this festival. "Makfest" was for many years the only promoter of Macedonian music outside the country. It was an international festival within the former Yugoslavia, with many guest appearances by famous foreign music names, and after independence became the biggest domestic music brand. Because of good results, twice received recognition from FIDOF, and in 1997 year was also declared the festival of the year. The Makfest scene continues to launch new music stars.

Also, starting from 1987 year, in the city is held “Shtip Cultural Summer” – a month-long festival held by 1 July to 1 August in the cultural center “Aco Shopov”.

Every year, on 8 November, the event is held in Shtip “Pastramiade”.