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Sestos (, ) was an ancient city in Thrace. It was located at the Gallipoli peninsula on the European coast of the Dardanelles, opposite the ancient city of Abydos, and near the town of Eceabat in Turkey.
In Greek mythology, Sestos is presented in the myth of Hero and Leander as the home of Hero.
In 479 BC, after the Greek victory at the Battle of Mycale, Sestos was besieged by Classical Athens forces led by Xanthippus. The Greek siege was resisted by a joint force of Persian soldiers and the city's native inhabitants and endured the whole winter, however, food supplies were inadequate as the siege was unexpected, and the city's garrison suffered from famine. The garrison subsequently capitulated and the Persian soldiers were imprisoned. Artayctes, the Persian governor of Sestos, had escaped, but was captured and crucified. However, Athenian influence over Sestos lapsed briefly, according to Plutarch, as Cimon retook the city in a second campaign at some point between 478 and 471.
Sestos became a member of the Athenian-led Delian League, and was part of the Hellespontine district. The city contributed a phoros of 500 Ancient drachma annually from 446/445 to 435/434, after which Sestos provided 1000 drachmas until 421/420. At Sestos, a 10 per cent tax was levied on westbound, non-Athenian, merchant grain ships. The city served as a base for the Athenian fleet until it was occupied by forces led by Lysander in 404, during the Peloponnesian War. Sestos' population was briefly expelled and replaced by Spartan settlers, but the city's native inhabitants were permitted to return to the city soon after.
During the Corinthian War, Sestos was occupied by Athenian forces led by Conon in 393, and the city came under the control of Ariobarzanes, Satrap of Phrygia. In 365, an attack on Sestos by Cotys I, King of Odrysian kingdom, was repelled with the aid of Timotheus, for which Athens was awarded with Sestos and Krithotai in the same year. A cleruchy was established at Sestos in 364, but the city was conquered by Cotys I after a surprise attack in 360, and a Thracian garrison was established. The Athenian general Chares seized Sestos in 353 and carried out andrapodismos whereby the male population was killed and women and children were enslaved; the city was repopulated by Athenian cleruchs.
The city was seized by Philip V, King of Macedonia, in 200 BC, and remained under Macedonian control until the conclusion of the Second Macedonian War in 196 with the Peace of Flamininus, which proclaimed Sestos a free city. In 196 BC, during the Roman–Seleucid War, Sestos surrendered to Antiochus III, Basileus of the Seleucid Empire, who refortified the city in 191 in preparation for a Roman attack, only for the city to surrender to Gaius Livius Salinator in 190. At the end of the war, the Treaty of Apamea of 188 awarded Sestos to the Attalid dynasty. By the end of the Hellenistic period, the offices of gymnasiarch and of ephebarch, with responsibility for the neoi (young) and Ephebos (adolescents), are attested at Sestos.
By late antiquity, the harbour of Sestos had silted up. In 447 AD, Sestos was sacked by the Huns. The city was damaged by an earthquake during the reign of Emperor Zeno in 478 AD. In the 6th century, according to Procopius' De Aedificiis, Emperor Justinian I refortified Sestos.
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