- the second largest river in North Macedonia, joining Vardar river after Štip. Roads follow the entire flow of Bregalnica around Štip and this is a very scenic drive.
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Емир Ќучук Султанов мост
This historic stone bridge has spanned the Bregalnica River since 1672. During World War I, this bridge crossed a line between Serbian-controlled territory and Bulgarian-controlled territory.
Црква „Свети Архангел Михаил Главатов“
One of the most valuable medieval monuments of Štip, this church was built in 1332 by Serbian nobleman Hrelja. It lost its frescoes during the Ottoman era when it was converted into a mosque. The church is cross-shaped and capped by a single dome. In 2000, it received a new marble iconostasis.
Саат-кула
This tower was built in 1650 as a guard tower. It was later adapted into a clock tower. Also known as Bey's Tower, it stands among mainly houses. The tower features a tall spire.
Меморијален комплекс на паднатите борци на револуцијата
On the Isar hill above the city is this monument to the partisans who perished in the National Liberation War of Macedonia. It consists of several separate elaborately carved blocks standing alongside each other. The site was built from 1969 to 1973. Inscribed here are 814 names of fallen soldiers from Štip and its surroundings.
Црква „Свети Архангел Михаил Главатов“
Not to be confused with the larger and better known Saint Michael church, this small church dates from 1389. Fragments of its original frescoes survive in the apse, while its icons date from the 19th century.
Исар; Štip Fortress
Above the confluence of the Bregalnica and Otinja rivers, these fortress ruins overlook Štip and its surroundings from a strategic point. The original date of its construction in unknown, though today's ruins likey date from the Serbian Empire. Varying amounts of walls and foundations survive today. A cross was erected among the ruins and it is illuminated at night. Several churches were built on the slopes below the fortress. This includes the churches of Saint Michael the Archangel, Saint Nicholas, and Saint John the Bapist, among a couple of others.