1.Dorostolon on the Danube
Ancient Durostorum, called Dorostolon or Dristra by the Byzantines and Drastar by the Bulgarians, was the easternmost of the great towns on the south bank of the Danube. Under the First Empire it was a patriarchal seat, and some chroniclers say that Simeon took refuge here during the Hungarian invasion. Its position — facing the steppe and at the head of the roads into the Dobruja and to the Black Sea coast — made it the key to north-eastern Bulgaria.
2.The Siege of Sviatoslav (971)
After the fall of Preslav in April 971 John Tzimiskes marched on Drastar, where Prince Sviatoslav of Kiev had his main forces. Shaken by the loss of the capital, the prince, according to Skylitzes, put to death 300 Bulgarians suspected of sympathy for the Byzantines and chained thousands of others for fear of a rising. On 25 April the emperor drew up his army before the city — infantry in the centre, cavalry on the wings — and battle was joined.
A three-month siege followed. Sviatoslav had a ditch dug around the walls, while Byzantine triremes with Greek fire and supply ships appeared before the city, cutting the river route. The miniatures of the Madrid Skylitzes show horsemen with long lances riding into the fortress — probably Bulgarians, since the Rus' had no cavalry. Worn down by hunger, Sviatoslav made peace and left the Bulgarian lands.
3.Under Byzantine Rule: Nestor and the Pechenegs (971–1185)
After the war Tzimiskes organised the lands on both banks of the Danube into military districts, and Drastar became the chief city of the province later called Paristrion, under a duke and later a katepano. In the Byzantine church hierarchy Dorostolon was a metropolitan see with five suffragan bishoprics.
The city was at the heart of the last great upheaval of the eleventh century. Around 1073 the emperor sent the vestarches Nestor, a Bulgarian by birth who had made his career in Constantinople, to Drastar as katepano. The next year Nestor rose against Michael VII, and the rebellious people of Drastar and the other Danube towns pushed far to the south, as far as eastern Thrace, but the movement ended in failure. By around 1086 Byzantine authority in Drastar and the lands east along the Danube had collapsed: the Pecheneg chief Tatous, also called Chalis, installed himself in the city, with Sesthlav and Satzas nearby, and the local leaders made common cause with them against the empire.
4.Ivaylo's Last Refuge (1279)
During Ivaylo's rising Drastar again became a battlefield. The Byzantine commander Michael Glabas Tarchaneiotes took Preslav and pursued Ivaylo's retreating forces through Cherven to Drastar, where they found a safe haven. After Ivan Asen III entered Tarnovo in 1279, he and the Byzantines sent an army against Ivaylo, who had shut himself up in the strong fortress. The siege lasted three months, but the city was not taken — evidence of how hard Drastar was to capture when its defenders resolved to hold it.
5.Dobrotitsa's City (c. 1370–1388)
In the second half of the fourteenth century Drastar was cut off from Tarnovo. Around 1370 the Dobruja despot Dobrotitsa, extending his domains westwards, annexed the fortress, and his son John Terter was probably made its governor. Coins with a monogram struck at the Drastar mint are linked by most scholars to him. The son, however, pursued his own policy: in 1376, in connection with the struggle for the throne of Constantinople, John Terter sided with Andronikos IV and killed the despot Michael Palaiologos, Dobrotitsa's son-in-law, at Drastar — wrecking his father's plans towards Trebizond.
6.The Price of Peace (1388)
In 1388 the grand vizier Ali Pasha crossed the Balkan range, took Shumen and Provadia and besieged Ivan Shishman in Nikopol. The Bulgarian tsar was forced to sue for peace, and the price was the surrender of Silistra. The Ottoman chronicler Neşri relates that the tsar came before the sultan near Yambol dressed in a shroud, prostrated himself and declared that he was handing over his finest city.
After Ali Pasha withdrew, Ivan Shishman refused to keep his promise and even set about fortifying Silistra. The answer was a new siege of Nikopol and a new defeat. Drastar fell to the Ottomans after stubborn resistance — according to Leunclavius the fortress was stronger than any other in the region.