According to certain data the bridge was built in the VI-th century, whereas in its present form it was raised upon the old foundation in the time of the Sultan Murat II in the first half of the XV century. It was built of well worked out stone blocks and has 12 semicircular arches. This monumental building has undergone larger repairs through the centuries, but today the bridge has still kept the primary shape and form.
As a result of the lack of more reliable sources and historical documents, two theories have evolved around the question when exactly the famous Stone Bridge on the Vardar was built and how old it is.
Some claim that it was erected during the Romaoian rule, in the middle of the 6th century, immediately after the disastrous earthquake of 518 when the ancient city of Skupi was destroyed. Much more likely, however, is the second theory, according to which the Bridge was built in the second half of the 15th century (between 1451-1469) under the patronage of sultan Mehmed II the Conqueror.
In historical sources, the Bridge was first mentioned in a document of the Isa-Bey Alaja (Colourful) Mosque in 874 (hijra), i.e. in 1469; the actual builders remain unknown. In its original shape, the Bridge had 13 arcs and was 329 steps long (or 213.85m.; one step is 65m.). Its total width was 6.33m. This is the Bridge seen and described by Jacobo Soronze, a Venetian who, on his way to Constantinople in 1575, stayed in Skopje.
Throughout the centuries, the Bridge was often damaged and 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 the fascists. But when the city was liberated the activation of the explosives was prevented and the Bridge was saved from a dreadful destruction.
The history of the Bridge is closely related to many incidents during the life of the Macedonian people under Turkish rule. In most cases, capital punishment was executed on the Bridge, which was then "decorated" with the heads of those who were executed. The body of a Macedonian revolutionary, Hristijan Todorovski - Karpos, after having been displayed on the Bridge for a while, was cut into pieces and thrown into the Vardar. In 1944, a large group of innocent Macedonian citizens were murdered on the Bridge by the German fascists before their withdrawal from Skopje.