The Museum in Kumanovo (National Institution Museum – Kumanovo / ционална установа Музеј – Куманово) is located in the former villa of the rich industrialist Zivko Stojiljkovic (Живко Стојиљковиќ), built in 1926 with a typical hallmark of the old city architecture.
The “Craft House” (Занаетчиски дом) or Kumanovo "Notre Dame" is the most recognizable landmark of Kumanovo city. It is work of the Russian engineer Vladimir Antonov (Владимир Антонов).
According to one story, Ahmed Niyazi Bey one of the leaders of Young Turk Revolution, after receiving a postcard of Versailles, also wanted to have a French-style estate.
Dame Gruev is a Macedonian national hero born in village Smilevo on January 19, 1871. He is one of the leaders of the national liberation movement.
Smilevo village is the birthplace of the Macedonian national hero Dame Gruev - one of the founders of IMRO (Internal Macedonian Revolutionary Organization – Macedonian: ВМРО).
The church dedicated to Saint Nikola in vilage Vevcani is a three-nave basilica with altar and inside parvis. The church was built in 1862 and consecrated in 1876.
„Peshta“Fortress is connected with the story of Kalesh Angya (Kales Angja, Калеш Анѓа) as a symbol of the Macedonian disobedience.
Kalishta Monastery complex is placed on the coast of Ohrid Lake in a natural rocky environment. This monastery complex - which is directly under the authority of the Archbishop of a Macedonian Orthodox Church, consists of four churches: two dedicated to the Nativity of Holy Mother of God (one old, in a cave and one new), a Church dedicated to Sts. Peter and Paul, the apostoles, and one dedicated to St. Athanasius the Great (in a cave).
Tsar Samoil fortress is considered one of the largest preserved fortifications in Macedonia. The fortress was first mentioned by the historian Titus Livy in the 3rd century BC, as a fortress of the city Lychnidos. Bigger more detailed description dates from the 5th century when the fortress was defended from tribal attacks during the Great Migration period.
The Pelince Memorial Museum was developed by the project of architect Georgi Konstantinov (Ѓорѓи Константинов) and the monumental mosaic facade is the work of the Macedonian contemporary artists Rubens Korubin (Рубенс Корубин) and Ilija Penushliski (Илија Пенушлиски).
Kostoperska Karpa (Bone Washing Rock, Костоперска Карпа) is archaeological site near the village Mlado Nagoricane (Младо Нагоричане) on 10 km northeast of Kumanovo and over international road that goes east to Kjustendil.