Skopska Crna Gora in the context of "Skopje Basin"

Kumanovo (Macedonian: Куманово [kuˈmanɔvɔ] ; Albanian: Kumanovë, Albanian definite form: Kumanova; also known by other alternative names) is the second-largest city in North Macedonia after the capital Skopje and the seat of Kumanovo Municipality, the largest municipality in the country. Kumanovo lies 340 metres (1,115 feet) 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. The Skopje Airport also serves Kumanovo.

It has many historical sites. One of its most important is the 4,000-year-old megalithic astronomical observatory of Kokino, located 30 km (19 mi) northeast of Kumanovo and discovered in 2001. It is ranked fourth on the list of old observatories by NASA.

Lovćen (Montenegrin Cyrillic: Ловћен, pronounced [lôːʋtɕen]) is a mountain and national park in southwestern Montenegro. It is the inspiration behind the names Montenegro and Crna Gora, both of which mean 'Black Mountain' and refer to the appearance of Mount Lovćen when covered in dense forests.The name Crna Gora was first mentioned in a charter issued by Stefan Milutin in 1276 and was used for several regions across medieval Serbian lands, including Skopska Crna Gora and Užička Crna Gora.

Mount Lovćen rises from the borders of the Adriatic basin, closing the long and twisting bays of Boka Kotorska and making the hinterland to the coastal town of Kotor. The mountain has two imposing peaks, Štirovnik; 1,749 m (5,738 ft) and Jezerski vrh; 1,657 m (5,436 ft).

Kaçanik Gorge (Albanian: Gryka e Kaçanikut; Serbian: Качаничка клисура, Kačanička klisura) is a gorge located in southern Kosovo, stretching between the town of Kaçanik and the Macedonian border, with the Lepenac river running through it. The Gorge splits the Šar Mountain range (Sharr) from the Skopska Crna Gora Mountain range (Karadak). During Ottoman rule, the gorge saw fierce fighting, and inspired songs still used today.

Anamorava (Albanian: Anamoravë), or Kosovo Pomoravlje (Serbian: Косовско Поморавље / Kosovsko Pomoravlje, "Morava Valley of Kosovo"), is a valley in Kosovo, in the southern part of the District of Gjilan surrounding the Morava e Binçës River. It stretches eastward to the Preševo Valley in southern Serbia. The mountains in this region, rising to an altitude of 1,000–1,200 metres (3,300–3,900 ft), border the Skopska Crna Gora region in north of Skopje. Gjilan, Kamenica, Novo Brdo and Viti are municipalities located in the region.

Dejan (Serbian Cyrillic: Дејан; fl. 1346 – c. 1366) was a magnate who served Serbian Emperor Stefan Dušan (r. 1331–55) as sevastokrator, and Emperor Uroš V (r. 1355–71) as despot. He was married to Emperor Dušan's sister Teodora, and possessed a large province in the Kumanovo region, east of Skopska Crna Gora. It initially included the old župe (counties) of Žegligovo and Preševo (modern Kumanovo region with Sredorek, Kozjačija and the larger part of Pčinja). Uroš V later gave Dejan the Upper Struma river with Velbužd (Kyustendil). Dejan rebuilt the Zemen Monastery, one of Dejan's endowments, among others, as he also reconstructed several church buildings throughout his province.

Dejan was one of the prominent figures of Dušan's reign and during the fall of the Serbian Empire after Dušan's death. Dejan is the progenitor of the Dejanović noble family, with his two sons, despot Jovan and gospodin Konstantin, also becoming powerful during the fall of the Serbian Empire and the ensuing Ottoman period.