Dimetoka (Didymoteicho) is an ancient Byzantine garrison city established on the banks of the River Erythropotamos, a branch of the Maritsa River. Close to its present-day location, emperor Trajan (98–117) founded the city of Plotinopolis. As the town was sacked by the Barbarians, emperor Iustinianos (527–565) abandoned the ancient city and created a new one close to the nearby River of Erythropotamos. The new city received its name “Didymoteicho” from the double wall that surrounded it, meaning twin fortification (“Didymóteichon”) in Greek. During the Ottoman period, the city was known as Dimetoka.

This strongly fortified Byzantine city had strategic importance and served as a defense line in Thrace to protect Constantinople, the imperial capital, from any attacks from Europe. Apart from its strategic importance, it became an imperial base during the Byzantine civil war. Backed by the Thracian nobles, Ioannes Kantakuzenos, the commander-in-chief and the chief lieutenant of the Byzantine emperor, was crowned emperor in the same city on October 26, 1341. Thus, for a certain period, Dimetoka became the de facto rival of the Byzantine capital. In the struggle against his rivals, Ioannes Kantakuzenos (Kantakuzenos VI) allied with Orhan, the Ottoman Sultan. The Ottoman forces had initially crossed to the Rumelian side to provide military aid to their Byzantine ally; later, however, they began to settle down permanently in the region. In 1354, Süleyman Paşa captured the strategically important town of Gelibolu. Following his death, the Ottoman advances in the region continued and the important cities of Edirne and Dimetoka were captured by Sultan Murad I. The conqueror of Dimetoka was an Ottoman commander called Hacı İlbey (1361).

Upon his accession to the throne, Murad I preferred to establish his main base and residence in this double-fortified city and then constructed a royal palace in the inner city. Until the rise of Edirne as the imperial capital, the sultan ruled his domains and coordinated his military operations in the Rumelia from his palace in Dimetoka. During this period, the entire city witnessed rapid urbanization, and new residential areas appeared outside the original intramural settlement. A completely new and typical Ottoman city developed in the vast plains around the old Byzantine town.

During the reign of Murad I, some neighborhoods were established in the new settlement areas, especially around Köprü Kapısı, the city gate at the south-west part of the city. The urbanization of the south-east zone, marked by the city gate called Çarşı Kapı, was relatively slow and just one neighborhood was established during the fourteenth century. In the subsequent century, this part of the city also became more urbanized with the emergence of new neighborhoods. Some, such as the Mahalle of Cüneyd Abdal, served as the residential quarters for the local Ottoman administrators and colonizing dervishes. 

Through to the end of the fourteenth century, the facade of the city changed with new buildings. The Mosque of Bayezid I and the marketplace became the center of the city, and shops and a bazaar clustered around them. Bayezid I himself financed the erection of a dervish lodge in the neighborhood of Ahi Denk (Denek) and endowed the revenues of several shops in the marketplace to cover its expenses. The same sultan also funded a water conduit to meet the city’s water demands.

The mosque and religious school (madrasa) constructed by Oruç Bey in the fifteenth century became another center of the Dimetoka. The madrasa of Oruç Bey has historical importance as the first madrasa of the city and one of the oldest of the Rumelia. Following a setback during the period of Interregnum, the Ottomans made further investments in education, cultural activities and public works. Similar to the contribution of Oruç Bey, the new buildings constructed by Karagöz Bey contributed to the rise of new residential quarters in different parts of the city. He erected a new mosque and the second madrasa of Dimetoka. All these edifices contributed to the cultural life and the education of the city.

A considerable population lived in the 17 neighborhoods of Dimetoka. While around 1500–2000 non-Muslims resided in the inner city during the first half of the fifteenth century, this number shrank to 565 by the end of the same century. This one-third decrease in the nonMuslim population may be somehow related to increased migrations to newly conquered Istanbul. As may be recalled, Dimetoka had served as the main base for one of the rival emperors during the Byzantine civil war. As for the Muslim population of the city, 1750– 1755 Muslims lived in the city in the late fifteenth century, while the total population was around 2400–2500.

To sum up, the small Byzantine garrison city in Thrace did not lose its importance under Ottoman rule. On the contrary, it became one of the most important headquarters of the Ottoman advances into Rumelia. Until the rise of Edirne, it served as a capital for Murad I and was rapidly urbanized with the establishment of new residential quarters outside the inner city and later further urbanized by the edifices of Yıldırım Bayezid and Oruç Bey erected in different parts of the city. Almost a century later, Dimetoka turned into a traditional Ottoman city with its mosques, madrasa, marketplace, shops and bathhouses.