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.

Vranje is a city and the administrative center of the Pčinja District in southern Serbia. The city has a population of 83,524 inhabitants, while the urban area of the city has 60,485 inhabitants.

Vranje is the first city from the Balkans to be declared UNESCO city of Music. It is on located on the Pan-European Corridor X, close to the borders with North Macedonia and Bulgaria. The Eparchy of Vranje is seated in the city and the 4th Land Force Brigade of the Serbian army is stationed here.

Vranje was an important Ottoman trading site. The White Bridge is a symbol of the city and is called "most ljubavi" (lovers' bridge) after the tale of the forbidden love between the Muslim girl Ajša and Christian Stojan that resulted in the father killing the couple. After that, he built the bridge where he had killed her and had the story inscribed in Ottoman Arabic. The city has traditional Balkan and Ottoman architecture.

The well-known theater play Koštana by Bora Stanković is set in Vranje.

Vranje is famous for its popular, old music, lively and melancholic at the same time. The best known music is from the theater piece with music, Koštana, by Bora Stanković. This original music style has been renewed recently by taking different, specific, and more oriental form, with the contribution of rich brass instruments. It is played particularly by the Vranje Romani people.

Vranje lies close to Besna Kobila mountain and Vranjska Banja, locations with high potential that are underdeveloped. Other locations in and around Vranje with some tourist potential include Prohor Pčinjski monastery, Kale-Krševica, Markovo kale, Pržar, birth-house museum of Bora Stankovic.