Ancient history
In the area of today's Valandovo in ancient times there was a Roman settlement, as evidenced by the discovered Roman mosaics and other archaeological materials in various parts of the city. Forty archeological sites were discovered on the territory of the Municipality of Valandovo, among which the ancient town of Isar is more important, near the village of Marvinci, which is identified with the ancient town of Idomena, whose origin dates from the end of the 5th century BC. and was located on the road Thessaloniki - Belgrade. The city flourished in Roman times, but in the early 6th century it was destroyed by a strong earthquake.
After the disappearance of the ancient city of Isar, Valandovo grew into a significant strategic settlement in the Valandovo valley. Some source materials and legends say that the ancient city on the foundations of which today lies Valandovo, in the early Byzantine period was mentioned as Micro Constantinople (Little Constantinople)
Medieval history
The Slavs settled in Valandovo and its surroundings at the end of the 6th century or at the beginning of the 7th century. At that time, great changes were noticed, both in terms of the structure of the population, and in the change of the toponyms of the settlements. In written sources the city was first mentioned in the 10th century as Wallander. But that does not mean that Valandovo as a settlement did not exist before. The archeological findings in the city are confirmation. The name "Wallander" was derived from the beautiful location of the city in the valley. Beautiful valley or good valley, in the Old Slavic language meant "valjan dol" ("valandol" or Valandovo). The beautiful Valandovo valley also had the epithets: "golden valley", "green valley", etc.
In medieval Valandovo was also mentioned with the name Alavandovo, meaning "flower city" ("city of flowers"). The city was mentioned under this name in a church charter of the Serbian Tsar Dusan from 1349. From the word "Alavandovo", by dropping the first letter "a" and through metathesis of the first syllables, the name Valandovo was obtained.
Modern history
Valandovo in the early twentieth century
Valandovo in its centuries-old history has had many ups and downs. The city has repeatedly suffered from natural cataclysms (earthquakes, fires, floods, epidemics, etc.) as well as from military actions of foreign invaders in this area. The 19th century is very important in the history of the city of Valandovo, when thanks to its convenient location it reached great development. According to legend, trade was developed in the city at that time. The following were exported: cattle, hides, trout, oil, wool, silk, pomegranates, grapes and other agricultural products, mainly in Thessaloniki.
In the 19th century Valandovo was a very important transit-traffic place. Traders and tenants traveled daily on the north-south roads, in caravans and carts loaded with merchandise. This greatly contributed to the revival of economic activity in Valandovo, to the development of trade and crafts.