The area around the town was inhabited in Neolithic times. It was later an important Thracian and Hellenistic town, sacked by the Romans in 204 BC. In the early 2nd century, the Roman emperor Trajan created a new city between the two hills surrounding the town and named it Plotinopolis after his wife Pompeia Plotina. The city would later be one of the most important towns in Thrace, having its own assembly. The ruins of the ancient city are now known as the Kale, after the Turkish for "castle". In 1965, a solid gold bust of Septimius Severus was found on the site of Plotinopolis and is now in the museum at Komotini.
The city had been built in a very strategic position, because it had for exloitation a very fertile plain and also controlled a passage of Erythropotamos, through which passed a branch of the via Egnatia leading in the middle and upper valley of Evros river and on the shores of the Black Sea.
According to F. A. Giannopoulos, Didymoteicho was probably built in the 6th century by Justinian I to replace Plotinopolis, whose exposed lowland location made it hard to defend. It seems that already in the 7th century, Plotinopolis had been abandoned in favour of the new site. The fortress was captured by Krum of Bulgaria in 813, but in 879 it was a bishopric whose incumbent, Nikephoros, participated in the Ninth Council of Constantinople. A century later, it served as a place of exile for the general and rebel Bardas Skleros, who unsuccessfully tried to oust Byzantine Emperor Basil II.
Didymoteicho briefly became the seat of a short-lived lordship within the Latin Empire after the Fourth Crusade. In the early 13th century, the town was fought over by Latin crusaders, members of the Angelos family, the Bulgarians, the Despotate of Epirus and finally the Empire of Nicaea, that returned Didymoteicho to Byzantine Greek control by capturing it around 1243 during the reign of John III Doukas Vatatzes. After the Byzantine reconquest of Constantinople in 1261, Didymoteicho became the most important city in Thrace.
During the Byzantine civil war of 1341–47, it served as the base of John VI Kantakouzenos. The lower city was destroyed during the war and rebuilt in 1342. After the war, the city became the centre of the Thracian appanage of Matthew Kantakouzenos, who provided it with strong fortifications. The city was also the birthplace of emperors John III Doukas Vatatzes and John V Palaiologos.
Didymoteicho was captured by the Ottoman Turks in 1359 and again, this time permanently, in 1361. The Battle of Demotika, the Ottomans' first victory in Europe, was fought before the city in 1352 during yet another Byzantine civil war.
The city—known as Dimetoka or Demotika under Ottoman rule—was probably captured by the Ottoman commander Hadji Ilbeg. It soon became the seat of the Ottoman court under Murad I, until the conquest of nearby Adrianople a few years later. It nevertheless remained a "favourite resort of early Ottoman rulers" due to its rich hunting grounds even after the capital moved to Adrianople and Constantinople. As such the city was rebuilt, with the Byzantine walls repaired and a royal palace constructed, and beautified, an effect still evident in 1443, when the French traveler Bertrandon de la Broquiere visited it. Bayezid II was born there and was on his way there to retire after abdicating in favour of his son, Selim I, when he died (probably of poison).
The Ottoman traveler Evliya Çelebi visited the town in 1670. The town was the seat of a kadi and administrative centre of the local district (nahiye). Evliya also provides a description of the fortress. The upper fortress, where the disused royal palace was located, measured some 2,500 paces in circumference, with double stone walls and "a hundred" towers; the sole Muslim living there was the commander, the rest of it, some 100 households, being inhabited solely by non-Muslims. The citadel within it (Iç Kale) was arranged on two levels, one of which was known as the "Maiden's Castle" (Kız Kalesı). The outer town (Varoş) counted 600 multi-storeyed houses and was divided into 12 wards (mahalle). There were several mosques and mesjits, of which the Bayezid Mosque was the most important, as well as four madrasahs, one of which was established by Sultan Bayezid I. From Evliya's references, the area of Didymoteicho appears to have been a major centre of the Bektashi dervishes. Of the local hamams, the most notable was the so-called "Whisper Bath" (fısıltı hamamı), with its "Ear of Dionysus"; it survived at least until the 1890s. The town had a marketplace but no bezesten; its chief produce were grapes and quinces, but also local pottery and glassware, which had a great reputation.
Swedish king Charles XII stayed in the town from February 1713 to October 1714 after his flight from the Battle of Poltava, but otherwise the town became an unimportant provincial backwater in early modern times.
In 1912 the town was briefly occupied by the Bulgarians during the First Balkan War, only to return to the Ottomans a year later. The Ottoman Government offered the city to Bulgaria in 1914, as a reward for entering World War I on the side of the Central Powers. Under the terms of the 1919 Treaty of Neuilly, Didymoteicho, along with the rest of Western Thrace,[9] came under the temporary management of a multinational Entente military force led by the French General Charles Antoine Charpy. In the second half of April 1920, as a result of the San Remo conference of the leaders of the main allies of the Entente powers (except USA), the region of Western Thrace was annexed by Greece. The Second World War devastated Didymoteicho.
Today, Didymoteicho - like the cities of Komotini and Xanthi, and much of the Xanthi and Rhodope regional units - is home to members of Greece's Turkish-speaking Muslim minority population (see Western Thrace Turks). Like the Pomaks of East Macedonia and Thrace the Turkish population of Didymoteicho dates to the Ottoman period and unlike the Turkish Muslims and Greek Muslims of Greek Macedonia and Epirus was exempted from the 1922-23 Greek-Turkish population exchange following the Treaty of Lausanne.
Source: wikipedia.org