Skopje is the capital and largest city of the Republic of Macedonia with about a third of the total population. It is the country's political, cultural, economic, and academic centre. It was known in the Roman period under the name Scupi.
The site of modern Skopje has been inhabited since at least 4000 BC. Remains of Neolithic settlements have been found within the Skopje Fortress. The earliest people in Skopje Valley were probably the Triballi. Later the area was populated by the Paionians, but in the 3rd century BC, Skopje and the surrounding area was invaded by the Dardanians. Scupi, the ancient name for Skopje, became the capital of Dardania, which extended from Naissus to Bylazora in the second century BC. Roman expansion east brought Scupi under Roman rule as a colony of legionnaires, mainly veterans of the Legio IIV Claudia in the time of Domitian (81-96 AD). However, several legions from the Roman province of Macedonia of Crassus' army may already have been stationed in there around 29-28 BC, before the official imperial command was instituted. Shortly afterwards it became part of the province of Moesia during Augustus's rule. After the division of the province by Domitian in 86 AD, Scupi was elevated to colonial status, and became a seat of government within the new province of Moesia Superior. The district called Dardania (within Moesia Superior) was formed into a special province by Diocletian, with the capital at Naissus. From 395 AD, it passed into the hands of the Byzantine Empire. Scupi was probably a metropolitan seat during the middle of the 5th century.
At that time Skopje was the capital of Kosovo as an Ottoman vilayet. During the Ottoman Tanzimat (1839–76) reforms, nationalism arose in the Empire and in 1870 a new Bulgarian Orthodox Church was established and its separate diocese was created, based on ethnic identity rather than religious principles. The Christian population of the bishopric of Skopje voted in 1874 overwhelmingly, by 91% in favour of joining the Exarchate. In 1893, the Internal Macedonian Revolutionary Organization was established in Thessaloniki by a small band of anti-Ottoman Macedono-Bulgarian revolutionaries, who considered Macedonia an indivisible territory and claimed all of its inhabitants "Macedonians", independently of their religion or ethnicity. In 1903 an organized revolt against the Ottoman Empire was carried out by the IMRO. Its revolutionary network in Skopje region was not well-developed and the lack of weapons was a serious problem. At the outbreak of the uprising the rebel forces derailed a military train. On 3 and 5 August respectively, they attacked a Turkish unit guarding the bridge on the Vardar river and gave a battle in the "St. Jovan" monastery. In the next few days the band was pursued by numerous Bashibozuks and moved to Bulgaria. The Ottomans were ultimately expelled from the city on 12 August 1912 when 15,000 Albanians marched on Üsküb.
On 11 March 1943, Skopje's entire Jewish population of 3,286 was transferred by Bulgarian occupying forces to the Nazis and deported to the gas chambers of Treblinka concentration camp in German-occupied Poland. This was in stark contrast to the way Bulgaria handled its own Jewish population.
Until 1991 Skopje was the capital of the Socialist Republic of Macedonia. The city expanded and the population grew during this period from just over 150,000 in 1945 to almost 600,000 in the early 1990s. Continuing to be prone to natural disasters the city was flooded by the Vardar River in 1962 and then suffered considerable damage from a major earthquake measuring 6.1 on the Richter scale, which killed over 1,000 people and made another 120,000 homeless. and numerous cultural monuments were seriously damaged. A major international relief effort saw the city rebuilt quickly, though much of its old neo-classical charm was lost in the process. The new master plan of the city was created by the then leading Japanese architect Kenzo Tange. The ruins of the old Skopje train station which was destroyed in the earthquake remain today as a memorial to the victims along with an adjacent museum. Nearly all of the city's beautiful neo-classical 18th and 19th century buildings were destroyed in the earthquake, including the National Theater and many government buildings, as well as most of the Kale Fortress. International financial aid poured into Skopje in order to help rebuild the city. As a result came the many modern (at the time) brutalist structures of the 1960s, that can still be seen today, such as the central post office building and the National Bank, as well as hundreds of now abandoned caravans and prefabricated mobile homes. Fortunately, though, as with previous earthquakes, much of the old Turkish side of town survived.
Skopje’s eateries are plentiful and offer a diverse range of local and international flavors. International cuisine is well represented in Skopje with Chinese, Italian, Indian, Greek, Mexican, Middle Eastern and French restaurants all found within the city center. In addition, pizza and fast food places abound, as do small bakery cafes selling pastries such as the ubiquitous burek (a flaky filo pie stuffed with meat, cheese or spinach).
- The Skopje Fortress, commonly referred to as Kale Fortress, or simply Kale (from kale, the Turkish word for 'fortress'), is a historic fortress located in the old town. It is situated on the highest point in the city overlooking the Vardar River. The fortress is depicted on the coat of arms of Skopje, which in turn is incorporated in the city's flag. The first fortress was built in 6th century and was constructed with yellow limestone and travertine and along with fragments of Latin inscriptions, assert the idea that the material for the fortress originated from the Roman city of Skupi, which was completely destroyed by an earthquake in 518. The fortress is thought to have been built during the rule of emperor Justinian I and constructed further during the 10th and 11th centuries over the remains of emperor Justinian's Byzantine fortress which may have been destroyed due to a number of wars and battles in the region, such as that of the uprising of the Bulgarian Empire against the Byzantine Empire under the rule of Peter Delyan. Not much is known about the Medieval fortress apart from a few documents which outline minor characteristics in the fortress' appearance. The fortress was partially destroyed yet again by an earthquake in 1963 but was not reconstructed until recently.
- The Church of Holy Salvation is a Macedonian Orthodox Church in Skopje. It is situated east of Kale Fortress. The church was built in the mid-16th century and is three-nave, with the middle vessel arched and flat pages covered with gains in domes. In the west is the gallery for women. On the south wall, above the present level of the floor during the repair of the church year 1963-64 was discovered a flat painting dating from the 16th-17th century. During the 19th century the church was given the inal look. In 1824 the iconostasis was completed and in 1867 it was part of the throne icons. The iconostasis and icons were made by cooperatives and traders from Skopje.
- Porta Macedonia is a triumphal arch located on Pella Square in Skopje. Construction started in 2011 and was completed in January 2012. The arch is 21 meters in height, and cost EUR 4.4 million. The arch is dedicated to 20 years of Macedonian independence and its outer surface is covered in 193 m2 of reliefs carved in marble, depicting scenes from the history of Macedonia. It also contains interior rooms, one of which has a function of state-owned souvenir shop, as well as elevators and stairs providing public access to the roof, allegedly intended as space for weddings. It is designed to match the almost equally tall statue of " Alexander the Great", erected in the capital's central square in summer 2011.
- The Mother Teresa Memorial House is dedicated to the humanitarian and Nobel Peace Prize laureate Mother Teresa and is located in her hometown Skopje. The memorial house was built on the popular Macedonia Street in the Centar municipality, on the very location of the once Sacred Heart of Jesus Roman Catholic Church, where Mother Teresa was baptized. It lies just east of the Ristiḱ Palace and the Macedonia Square. In the first three weeks, the memorial house was visited by 12,000 people.
- The Stone Bridge is a bridge across the Vardar River. The bridge is considered a symbol of Skopje and is the main element of the coat of arms of the city, which in turn is incorporated in the city's flag. The Stone Bridge connects Macedonia Square, in the centre of Skopje, to the Old Bazaar. The bridge is also less frequently known as the Dušan Bridge after Stephen Uroš IV Dušan of Serbia. The current Stone Bridge was built on Roman fondations under the patronage of Sultan Mehmed II the Conqueror between 1451 and 1469. Throughout the centuries, the Stone Bridge was often damaged and then repaired. There is historical evidence that it once suffered during the great earthquake of 1555 which heavily damaged or destroyed four pillars. In 1944, explosives were placed on the bridge by Nazis. When Skopje was liberated, the activation of the explosives was prevented and the bridge was saved from destruction. Some executions have also taken place on this bridge, such as the execution of Karposh in 1689.