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Photo: Македонец, CC BY-SA 4.0 via Wikimedia Commons
West of Kumanovo within the Skopska Crna Gora mountain range is this 14th-century monastery. Built atop the foundations of an older church, Serbian King Stefan Dušan began reconstructing the monastery and it was completed by his son Stefan Uroš V in 1357. The monastery's church, dedicated to the Ascension of the Virgin Mary, is in the Byzantine style and has one larger dome and four smaller domes. Its roof was removed by the Ottomans in the 18th century and put atop the Eski Mosque, though it was renovated in the 1920s and 1930s. The village is now primarily Albanian with a small Serb minority. The monastery was occupied by Albanian insurgents during the 2001 conflict who damaged some of the interior frescoes and stole various objects.
The Monastery of the Most Holy Mother of God, commonly known as Matejče (Матејче) or Matejić (Матејић), is a 14th-century Orthodox monastery located in the village of Matejče on the slopes of Skopska Crna Gora, near Skopje and Kumanovo.
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Татар Синан Бег Џамија
Also known as Eski (old) Mosque, this Ottoman-era mosque was built in 1532. It features one dome and one minaret and its courtyard contains some old graves.
Црква „Св. Троица“
This 1902-built church was established by the population belonging to the Serbian church as they were not admitted to St Nicholas which was controlled by the Bulgarian Exarchate. Today, both of these churches are Macedonian Orthodox. The blueprints of the church were done by a Russian architect. The iconostasis was completed with funds donated by Queen Draga of Serbia.
Црква „Св. Никола“
This large, white church is surrounded by arcades and has a rich interior with galleries, frescoes, and furniture. According to an inscription on the south entrance, it was built in 1851 on the same site as a prior church (with the same patron saint) in the Varoš neighborhood. Designed by noted church architect Andrej Damjanov, it is the main church of the city of Kumanovo.
Спомен костурница
The Memorial Ossuary of Kumanovo is a monument to the National Liberation War of Macedonia. Consisting of a female with raised hands holding a crown, the monument is the main feature of the municipality's coat of arms. It is situated on a hill north of the city-centre. A large memorial service occurs here every 11th of October.