Prilep is the fourth largest city in North Macedonia. It has a population of 66,246 and is known as "the city under Marko's Towers" because of its proximity to the towers of Prince Marko.

The name of the city comes from the Macedonian word "Прилеп" (meaning "sticky") and it showcases how the buildings were first built there, being near one another next to the Marko's Towers.

The main square in Prilep is called "Alexandria", in honor of Alexander the Great. The reconstruction of the square began in 2005 and it was completed in 2006. The reconstruction cost 700.000 Euros and its investor was the city of Prilep. During the reconstruction the monument of Alexander the Great was erected, among the other things.

The most important ancient monument is the old city of Styberra situated on Bedem hill near Čepigovo, in the central region of Pelagonia. As early as the time of the Roman–Macedonian wars, this city was known as a base from which the Macedonian king Perseus of Macedon set out to conquer the Penestian cities. An important site in the area is Bela Crkva, 6 km (4 mi) west of Styberra, where the town of Alkomenai was probably located. It was a stronghold of the Macedonian kings after it was rebuilt in the early Roman period and was at the Pelagonian entrance to a pass leading to Illyria. Part of the city wall, a gate, and a few buildings of the Roman period were uncovered here in excavations. All recent finds from these sites are in the Museum of the City of Prilep.

Skopje is the capital and largest city of the Republic of Macedonia. It is the country's political, cultural, economic, and academic center. Skopje is located on the upper course of the Vardar River, and is located on a major north-south Balkan route between Belgrade and Athens. It was known in the Roman period under the name Scupi.

The territory of Skopje has been inhabited since at least 4000 BC; remains of Neolithic settlements have been found within the old Kale Fortress that overlooks the modern city centre. On the eve of the 1st century AD, the settlement was seized by the Romans and became a military camp. When the Roman Empire was divided into eastern and western halves in 395 AD, Scupi came under Byzantine rule from Constantinople.

Being the capital of the Republic of Macedonia, Skopje is home to the largest cultural institutions of the country, such as the National and University Library "St. Kliment of Ohrid", the Macedonian Academy of Sciences and Arts, the National Theatre, the National Philarmonic Orchestra and the Macedonian Opera and Ballet. Among the local institutions are the Brothers Miladinov Library which has more than a million documents, the Cultural Information Centre which manages festivals, exhibitions and concerts, and the House of Culture Kočo Racin which is dedicated to contemporary art and young talents.

The Skopje Jazz Festival has been held annually in October since 1981. It is part of the European Jazz Network and the European Forum of World Wide Festivals. The artists' profiles include fusion, acid jazz, Latin jazz, smooth jazz, and avant-garde jazz. Ray Charles, Tito Puente, Gotan Project, Al Di Meola, Youssou N'Dour, among others, have performed at the festival. Another music festival in Skopje is the Blues and Soul Festival. It is a relatively new event in the Macedonian cultural scene that occurs every summer in early July. Past guests include Larry Coryell, Mick Taylor & the All-Stars Blues Band, Candy Dulfer & Funky Stuff, João Bosco, The Temptations, Tolo Marton Trio, Blues Wire, and Phil Guy.