The Romans built a fortress in AD 29 on the site of an earlier Thracian settlement and kept its name, Durostorum (or Dorostorum). It became an important military center of Moesia, and grew into a city at the time of Marcus Aurelius. In 388, Durostorum became the seat of a Christian bishopric and a center of Christianity in the region. Roman general Flavius A�tius was born in the town in 396. After the Roman Empire split into the Eastern and Western empires, the town (known as ???????????, Durostolon in Byzantine Greek) became part of the Byzantine Empire. As part of the Bulgarian Empire Durostolon then became known as Drastar by the Bulgarians in Medieval times.
Around the end of the 7th century, the town was incorporated in the First Bulgarian Empire and the bishop of Drastar was proclaimed the first patriarch of Bulgaria. In 895 during the Bulgarian-Hungarian War of (894-896), the Hungarians who acted as Byzantine allies besieged the Bulgarian army under the personal command of Simeon I the Great in the fortress of the town but were repulsed. On the next year the Hungarians were decisively defeated in the battle of Southern Buh.
The town was captured by the forces of Sviatoslav I of Kiev in 969, but two years later it was besieged by the Byzantines during the Battle of Dorostolon. Having been ceded to the Byzantines, it was renamed Theodoropolis, after military saint Theodore Stratelates, who is said to have come to Emperor John I Tzimiskes' aid during the battle. In 976, Tsar Samuil restored Bulgarian rule in the region until 1001, when it was once again incorporated within the bounds of the Byzantine Empire.
In 1186, after the Rebellion of Asen and Peter, the town became part of the Second Bulgarian Empire.
In 1279 Emperor Ivailo was besieged by the Mongols in Drastar but after three-month siege the Bulgarians managed to break through.The town remained part of the Empire until the Ottoman conquest of Bulgaria in 1396. Throughout the
