According to tradition, the city was founded before the Trojan War but is mentioned for the first time by Herodotus. After the Roman occupation it became an important city in the province of Macedonia and seat of a confederation of five cities ("Pentapolis"). During this period several inhabitants received the Roman citizenship and occupied higher provincial dignities. The first attested bishop of the city is recorded as participating in the Second Council of Ephesus in 449.
In the early Middle Ages, Serres became the site of a major fortress built by the Byzantine Empire to guard the empire's northern frontier and the strategic Rupel Pass.The city's history was uneventful until the 10th century, being in the heartland of the Byzantine Greek world, until it was pillaged and briefly occupied by the Bulgarians. In 1185, the environs of the city were pillaged by a Norman invasion, and in the Battle of Serres in 1195/6 the Byzantines were defeated by the rebellious Bulgarian ruler Ivan Asen I. After the Fourth Crusade, Boniface of Montferrat took over the city, but shortly after Kaloyan of Bulgaria defeated the Crusaders of the Latin Empire and briefly annexed the city until it was retaken by the Crusaders in the early 1230s. According to George Akropolites, Kaloyan almost destroyed the city, reducing it from a sizeable city to a small settlement, centred around the fortified citadel, while the lower town was protected by a weak stone wall.[6]The city returned to Byzantine rule in 1246, when it was captured by the Nicaean Empire. By the 14th century, the city had regained its former size and prosperity, so that Nikephoros Gregoras called it a "large and marvelous" city. Taking advantage of the Byzantine civil war of 1341–47, the Serbs besieged and took the city on 25 September 1345. It became the capital of Stefan Dušan's Serbian Empire, but after Dušan's death in 1355 his realm fell into feudal anarchy, and Serres became a separate principality, initially under Dušan's Empress-dowager Helena and after 1365 by the Despot Jovan Uglješa. Jovan Uglješa maintained close political and cultural ties to the Byzantine court in Constantinople, and the Greek element rose again to prominence: local Greeks played a major role in his administration, which was carried out in Greek. After the 1371 Battle of Maritsa, the Byzantines under Manuel II Palaiologos (then governor of Thessalonica) retook Serres.
Serres fell to the Ottoman Empire on 19 September 1383—although the Ottoman sources give several earlier and contrsdictory dates, the date is securely established by multiple Greek sources. The city (Siroz in Turkish) and the surrounding region became a fief of Evrenos Beg, who brought in Yörük settlers from Sarukhan. Althougn never rising to particular prominence within the Ottoman Empire, Serres became also the site of a mint from 1413/14 on. The rebel Sheikh Bedreddin was executed in the city. In the early 16th century, Serres was visited by the French traveller Pierre Belon, who reported that the town was mainly inhabited by Greeks alongside German and Sephardi communities, while the people in the surrounding country spoke Greek and Bulgarian. In the aftermath of the Christian victory at the Battle of Lepanto in 1571, Turkish reprisals were directed at the Greek population, who had shown sympathy with the Western success and had sporadically risen up across Greece. The metropolitan cathedral of Serres was looted along with seven other churches, while land and land titles owned by the Monastery of St John the Baptist were confiscated.[9]In the 18th and early 19th centuries, Serres was an autonomous beylik under a succession of derebeys, within the Sanjak of Salonica.[8][10] At the end of the 18th century, Serres was a cotton producing area, exporting 50,000 balls of cotton to Germany, France, Venice and Livorno.[11] The metropolitan (Greek Orthodox bishop) Gabriel founded in 1735 the Greek School of Serres which he directed until 1745. The school was maintained by donations from wealthy Greek merchants, among them Ioannes Constas from Vienna with 10,800 florins and the banker and tragic leader of the Greek revolution in Macedonia Emmanuel Pappas, who donated 1,000 Turkish silver coins. Minas Minoides taught Philosophy and Grammar in 1815-19. The school operated also in the period of the Greek revolution under Argyrios Paparizou from Siatista. Serres became a regular province ca. 1846 as the Sanjak of Siroz of the Salonica Eyalet (later Salonica Vilayet).
In the early 20th century, the city became a focus of anti-Ottoman unrest, which resulted in the Ilinden-Preobrazhenie Uprising of 1903. A Bulgarian army, which was commanded by general Georgi Todorov captured Serres during the First Balkan War on November 6, 1912 but was forced to withdraw by Greek forces commanded by the King of Greece, Constantine I, during the Second Balkan War. The first officer of the Hellenic Army to enter Serres was infantry colonel Napoleon Sotilis, head of the Seventh Greek Infantry Regiment on July 11, 1913. Serres was temporarily occupied by the Central Powers in the First World War, eventually being liberated by Greek-French Entente forces, and after the fall of Greece in the Second World War, it was occupied by the Axis between 1941 and 1944. In 1943, Serres' Jewish population was deported by the Gestapo to the Treblinka death camp and exterminated.In the postwar years, the city's population grew substantially, and there was also a significant rise in the standard of living. The long-serving conservative Greek Prime Minister Constantine Karamanlis (in office from 1955 to 1963 and again from 1974 to 1980) was a native of Serres, and as a result its people could count on the support of the central Greek government in Athens. However, the villages in the plains around the city were not so lucky; the low prices of agricultural products led many people of these villages to immigrate, mostly to the United States and West Germany.
source: www.wikipedia.org