Pećinski crteš u blizini sela GabrovnicaSoutheast Serbia was inhabited during prehistoric times, which is evidenced by numerous traces of former human habitats such as cave drawings of horsemen in Gabrovnica near Knjaževac, traces of Neanderthal man on the site known as “Pećurski stone” near Sokobanja, sites “Bubanj” and “Velika humska čuka” near Niš etc.

In the classical period (1st century BC) the Roman military road called Via Militaris passed through this area, that linked Singidunum with Constantinople, today's Corridor 10, as evidenced by numerous forts and inns along this road.

The ancient chronicler Pliny (2nd century AD) records this space as part of the Roman province of Moesia inhabited by the Moesi, Thracians, Dardanians and Tribals.

The famous Roman emperor and general Flavius Valerius Constantinus (Constantine the Great), was born in this region in 274. He is known in world history as a visionary who issued The Edict of Milan on religious tolerance in 313, after which the persecution of Christians in the Roman Empire was stopped. At the time of Constantine, especially after the Edict of Milan in 313, Christianity came to inner Dacia, and in the second half of the fourth century the Episcopal chair in Remesiana (Bela Palanka) was established, with Bishop Nicetas. There are numerous ruins from this period in Niš: villas and mosaics at the archaeological site Mediana, a number of items, coins and sculptures of exceptional artistic value (a copy of the portrait – a bronze head of Emperor Constantine), which are exposed in the Archaeological hall of the National Museum. In the third century in Zaječar, the second of the sixteen emperors was born, Gaius Valerius Maximian.

Since the collapse of the Roman Empire, in the history of Southeast Serbia there were periods of Byzantine, Bulgarian, Serbian and Turkish rule.

In the 14th century, the Turks conquered this region and left behind valuable traces of material culture (Niš Fortress, the Turkish Bath in Sokobanja).

During the Ottoman rule, Pirot was an important place on the road to Constantinople, and when necessary, it was a military lodging and the meeting place of the Turkish army.
Manastir Sv. Trojica
In the second half of the eighteenth century, in 1761, the diocese of Niš and Pirot was established, based in Pirot, as a separate unit within Sofia Metropolis. The crisis and the fall of the First and the Second Serbian Uprising had grave consequences in this region. In 1833, this area was finally liberated and became part of Prince Miloš’s Serbia.

Southeast Serbia lived peacefully until 1876, when Serbia and Montenegro entered the war with the Turks, helping the Serbian rebels in Bosnia and Herzegovina, who started an uprising in 1875. These areas once again become the scene of bloody battles with the Turks, who were braking out from the area of Vidin.
Standing in the war centre of the Balkans, this region participated in two Balkan wars and in both world wars in the last century.
With its rich history, Southeast Serbia is today a tourist destination with a rich cultural and historical heritage.