The earliest known documented sources that point out to the existence of a merchant quarter on the bazaar's territory date back to the 12th century. During the Ottoman rule with the city, the place underwent a rapid development to become city's main economic and merchant centre, evidenced by about 30 mosques, numerous caravanserais and hans, as well as other Ottoman buildings and monuments. The bazaar was heavily damaged by the earthquakes that occurred in 1555 and 1963, and the destructions caused during the First and the Second World War. Subsequently, it was reconstructed on several occasions and nowadays represents the only remaining cultural monument in the Republic of Macedonia, which has kept its multicultural heritage of different civilizations.
The Ottoman architecture is predominant in the Old Bazaar, although remains of the Byzantine architecture are evident as well, while the most recent reconstructions lead to the application of elements specific to the Modern architecture. Most of the buildings that once were used to host the travellers or as hamamsШаблон:Dn for the political dignitaries were transformed into museums and galleries, which today are used with the main purpose to host art exhibitions, concerts and other cultural events. Nowadays, however, the place and its proximity are still home to several mosques, türbes, two churches and a clocktower, that together with the buildings of the Museum of Macedonia and the Museum of Modern Art form the core of the modern bazaar. The Museum of the Skopje Old Bazaar, situated in Suli Han, includes collections of artifacts that evidence the life within the bazaar, its development, and the crafts that were practiced during its history.
On 13 October 2008, the Macedonian Parliament adopted a law recognising the Skopje Old Bazaar as a cultural heritage of particular importance for the country with a permanent protection. In early 2010, the Macedonian Government has commenced a programme for revitalisation of the Old Bazaar, which, in turn, includes restoration of several objects, providing support of the crafts, and aiming a further economic and cultural development of the site.
The earliest known archaeological findings revealed at the Kale Fortress testify that the surrounding area has been inhabited since 4,000 BC, while the earliest historical facts mention the Paeonians as the first people who settled up on this area.
Following the fall of the city of Scupi under Roman rule, numerous Roman buildings, such as temples, thermaes, and theatres were built inside the city, that subsequently promoted it as an important religious and cultural centre in the Roman Empire.
In 518, Scupi was heavily damaged by a devastating earthquake, which prompted the Byzantine emperor Justinian I to rebuild a new capital that was located distantly from the destroyed city. Nevertheless, the local population settled up on a hilly area, where, later, the emperor Justinian ordered the construction of the Kale Fortress.
During the reign of king Samuel, Skopje was given a particular strategic, political, economic, and cultural importance, so that the surrounding area of the Kale hill was embanked by the enactment of defensive walls, in order to keep the treasures that were present in the settlement. At the time, there was a gate named "Watertower Gate", which was built with the purpose to defend the city against the successive attacks by the Byzantine emperor Basil II in 1001.
After the fall of the First Bulgarian Empire under Byzantine rule in 1018, the emperor Basil II transformed Skopje into a capital of a theme and an episcopal see, whose bishop was elected for a four-year term. Following the death of Basil, his successor, Romanos III Argyros, undertook activities to reconstruct the Monastery of St. Georgi, which, according to the deed of the Serbian king Stephen Uroš II Milutin of Serbia from 1300, was situated on the hill called "Virgin", elevated on the bank of the river Serava, the place where today the Sultan Murad Mosque is located. It is said that the monastery, at the time, was one of the most reputable and decorated monasteries in most of the Balkans.
Skopje's bezisten, a covered market, was built in the 15th century by Gazi Ishak Bey, the Sultan's Skopje regent. It was destroyed by a fire in 1689 and was later rebuilt. The bezisten has looked the same since its renovation in 1899.
Skopje's clock tower, built in the 16th century on the foundations of an older edifice, is located just north of the Sultan Murad Mosque. Originally built of wood, the top was replaced with bricks in 1902.
The hexagonal tower was heavily damaged during the 1963 earthquake. It was soon fully repaired.
The Çifte Hamam (Turkish for 'double bath'), located in the centre of the old bazaar, was built in the 15th century under Isa Bey. The building is divided into two wings (hence the name 'double'): one for men and one for women. The layout of both sections are nearly identical.
The Çifte Hamam was used as a bathhouse until 1915. After suffering damages during the 1963 earthquake, it was repaired and has housed the Contemporary Art Gallery since then.
Daut Paşa Hamam
Daut Paşa, Grand Vesir of East Rumelia, constructed this hamam in the 15th century. The building consists of fifteen rooms covered by thirteen domes. The two largest domes covered the two changing rooms and the rest of the domes covered individual bathing rooms.
Since 1948, the Daut Paşa Hamam has housed the National Art Gallery.
Isa Bey Mosque
Situated on the outskirts of the bazaar, this mosque was built as a memorial for Isa Bey after his death. The mosque has two dominant domes and five smaller ones above the porch area.
Ishak Bey Mosque
Also known as the Decorated (Aladya) Mosque because of the floral decorations, inscriptions and coloured tiles found on its walls, the Ishak Bey Mosque was constructed in 1439 in the northern part of the Old Bazaar. The mosque's minaret rises 30 meters (98.4 feet). There is a türbe located behind the mosque.
Located on the highest hill in Skopje, overlooking the city and the river, the area upon which the fortress was built was first inhabited in prehistoric times, according to archaeological findings.
Most researchers believe that the fortress was first constructed in the 11th century.
Шаблон:Main One of the three remaining caravanserais in the Old Bazaar, the Kapan Han was built in the 15th century. The rooms in the upper floor were available to guests, while the ground floor was used as a stable to house the guests' horses and cattle.
The largest of the three remaining caravanserais, the Kurşumli Han (Turkish for 'Lead Inn') was built by Musein Odza, the son of a scientist at Sultan Selim II’s court, in the 16th century.
The roof of the inn was once covered in lead (hence the name), but was removed during World War I. The Kurşumli Han also has several small pyramidically-shaped domes. The building has a ground floor, which housed the cattle and horses, and a first floor, which housed the guests.
The attached mosque, built in the 17th century, and most of the hamam, built in the 15th century, were destroyed in the 1963 earthquake.
Today, the former han houses the statue collection of the Museum of Macedonia.
Mustafa Paşa Mosque
Шаблон:Main The Mustafa Paşa Mosque, built in 1492 by Mustafa Paşa on an older Christian site, stands above the Old Bazaar, near Kale Fortress. Considered one of the most elegant Islamic buildings in Macedonia, the complex includes the mosque, the tomb of Mustapha Paşa, the sarcophagus of one of his daughters, a fountain, and remnants of other buildings.
The mosque is square in shape and its largest dome is 16 metres (52.5 feet) in diameter. The porch is positioned on four marble pillars, decorated with stalactite, and covered by three small domes. The interior is decorated and includes calligraphic inscriptions. The minaret of Mustafa Paşa Mosque, rising 42 metres (137.8 feet) is made of limestone.
Mustafa Paşa is buried in the hexagonal marble türbe covered by a dome above a short eight-sided tambour. Umi, one of his four daughters, is buried in the decorated sarcophagus which includes Persian inscriptions on two of the four walls. The mosque courtyard is filled with roses and, due to its elevated location, offers a distinct view of the Old Bazaar.
Church of the Holy Salvation
Constructed in the 16th century on the foundations of an older church, half of the church was built underground as it was illegal under Ottoman rule for Christian buildings to be taller than Islamic buildings so mosques could dominate the city skyline. The church got its present appearance in the 19th century.
The church's iconstasis was carved in wood and is 10 metres (32.8 feet) long, 4.5 to 7 metres (14.8 to 23 feet) in height.
Revolutionary Goce Delčev is buried in a white stone sarcophagus in the church's courtyard.
The Stone Bridge, across the Vardar River, connects the Old Bazaar to Macedonia Square in the new part of the city. The bridge, built in the 15th century under Sultan Murad, was built of stone blocks as its name suggests, which has helped it survive the fires and earthquakes Skopje has seen. The Stone Bridge has had the same appearance since it was first built.
The bridge has 12 semicircular arches and is 214 metres (702 feet) long. During Ottoman rule, countless executions were conducted on the Stone Bridge.
The Suli Han was built under Ishak Bey in the 15th century. It has two floors with the upper having 54 rooms for the guests and the lower for the guests' cattle. It was fully repaired after sustaining heavy damaged during the 1963 earthquake.
The han today houses the Skopje Academy of Art and the Old Bazaar Museum.
Sultan Murad Mosque
Sultan Murad built this mosque in 1463, just south of where the clock tower would be built. The mosque has remained mostly undamaged through the fires and earthquakes Skopje has sustained.
The Sultan Murad Mosque is rectangular in shape, with a porch including four columns with decorated caplets, connected by arcades.
Yahya Paşa Mosque
The Yahya Paşa Mosque was built in 1504 for Yahya Paşa. During World War I, the mosque was used as a German weapons and ammunition production facility.
The mosque's minaret is roughly 50 metres (164 feet) tall. There are several tombs and a burial chamber in the Yahya Paşa Mosque's courtyard.