There are no reliable data about when and where the settlement was established, but the presumption is that it happened at the time of the Romans, Byzantium and the Slavs.

The first written record of Vranje was left by Ana Komnina - Greek royal lineage back in the XI century. Vranje is definitely became a part of the Serbian state 1207 when it was won by Stefan the First-Crowned.

In the First World War the Bulgarians occupied Vranje in 16th and 17th of October in 1915, and it was freed by the Serbian warriors of Solun’s front on 4th of October in 1918. In World War II the Germans entered the city on 9th of April, 1941, and surrendered it to the Bulgarian fascists on April the 22nd, 1941.

Vranje was liberated on 7th of September, 1944.

Cultural and historical monuments of Vranje:

- Marko’s kale, the remains of a medieval fortress, made on the ancient foundations. It is assumed that it was built by Justian the Byzantine emperor in the sixth century.
- Church of St. Nikola, foundation of brothers Balsic. Emperor Dusan gave it to Chilandar between 1343 and 1345.
- Church of Mucenica Petka Paraskeva, known as cross mosque. The Turks wanted to settle the two religions by putting the cross and crescent on the top of the minater.
- Hamam, an old Turkish bath, built at the end of the seventeenth century.
- Pasha’s Konak, built by Raif Bey Dzinic in 1765.
- Church Bogorodicino Uspenje, dating from the medieval Serbian state. Turks destroyed it, but it was rebuilt in 1820
- White bridge built in 1844. It is called "a bridge of love" because, according to legend, it was built in commemoration to unhappy love of the Turkish woman Aisha, and Serbian shepherd Stojan.
- Fountain Djerenka: legend says that the Turks built it as a monument to their favorite Djerzelez, who failed to win the heart of beautiful black eyed Serb women which, after him, was called - Djerenka.
- Church of Prepodobna Paraskeva - St. Petka, built in 1925, on the foundations of the old temple which belonged to Metochion Monastery Decani.
- Bora Stankovic House Museum, built around 1850. It was turned into a museum on 18th of June, 1967.
- Monument to the liberators of Vranje in 1878, known as Uncle Mitke, revelaed in 1903.
- Monument to victims of atrocities of the Bulgarian occupiers, built early in 1922.
- The monument dedicated to Bora Stankovic, unveiled on 7th of September, 1954.
- Monument dedicated to the revolution from 1985.
- Monument dedicated to the soldiers of wars of 1912-1918, built in 1988, in commemoration of the victims of the Balkan and First World War.

Events:

• Days of Carnations
• Bora’s Sunday
• Vanja’s Days
• Vranje spa