"Didymoteicho" is the modern Greek form of Διδυμότειχον, Didymóteichon, from δίδυμος, dídymos, "twin" and τεῖχος, teîchos, "wall".

In the early 2nd century, the Roman emperor Trajan created a new city on the banks of the Evros river, between two surrounding hills, near modern Turkish Uzunköprü, and named it Plotinopolis after his wife Pompeia Plotina.

The city had been built in a very strategic position, because it had for exploitation 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.

[3] Given the exposed lowland location of Plotinopolis, the site was soon abandoned in favour of the more recent fortress, a process that was possibly completed already in the 7th century.

[3] In summer 813, during his invasion of Thrace, the Bulgarian ruler Krum captured the town,[3] but in 879 it was a bishopric whose incumbent, Nikephoros, participated in the Ninth Council of Constantinople.

[3] A century later, the town served as a place of exile for the general and rebel Bardas Skleros, who unsuccessfully tried to oust Byzantine Emperor Basil II.

[12] In February 1205, however, the locals rose up in revolt in Didymoteicho, Adrianople and other cities, evicted their Latin garrisons, and acknowledged the suzerainty of the Bulgarian Tsar Kalojan.

Kalojan besieged Didymoteicho in early summer, and was on the point of taking the city when a relief army under Henry arrived.

Henry of Flanders managed to rescue the inhabitants as they were being taken prisoner to Bulgaria, but before he withdrew from the city, Kalojan ordered the town's fortifications razed, making it useless as a military base.

[4] Finally the Empire of Nicaea returned Didymoteicho to Byzantine control by capturing it around 1243, during the reign of John III Doukas Vatatzes.

The latter made Didymoteicho his main base and residence during the conflict, and the city remained a stronghold and was frequently visited by Andronikos III during his reign.

[4] The city also served as a secure place of exile and incarceration of the emperor's opponents, from his uncle Constantine Palaiologos in 1322 to the disgraced chief minister Theodore Metochites in 1328.

[4] During the Byzantine civil war of 1341–47, it served as the base of Andronikos III's chief lieutenant, John VI Kantakouzenos (r. 1347–1354), who was crowned emperor in the city on 26 October 1341.

With the aid of Umur Bey, ruler of the Turkish beylik of Aydin and owner of a considerable fleet, repeated attempts by the Bulgarian Tsar Ivan Alexander and Kantakouzenos' Byzantine opponents, headed by Alexios Apokaukos, were defeated, and the city remained in his hands throughout the conflict, serving as his main stronghold in Thrace.

[18] In 1352, it was assigned to John V Palaiologos (r. 1341–1391), but he quickly clashed with Matthew Kantakouzenos, and only after another round of warfare in 1352–57 did the city finally come into Palaiologan hands.

[19][18] 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 traveller Bertrandon de la Broquiere visited it.

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.

Under the terms of the 1919 Treaty of Neuilly, Didymoteicho, along with the rest of Western Thrace,[21] 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 the United States), the region of Western Thrace was annexed by Greece.

Didymoteicho is just 2 kilometers away from the Greek-Turkish border, and as a result it is home to many Greek military units and Hellenic Army training centers.

The famous 1991 George Dalaras and Lavrentis Machairitsas song Didymoteicho Blues (Greek: Διδυμότειχο Μπλουζ) pays homage to the personal stories and experiences of these soldiers while offering a more general commentary about life in the Army.