The history of Sestos is intertwined with that of Abydos, which was directly across the Hellespont. As the key crossing site, nearly every historic figure involved between Asia and Europe in ancient times spent time here. The Persians twice crossed from here to Abydos, first against the Persians and again by Xerxes in his famed invasion of Greece.
Kotys I conquered the city at one point and it was also contested by the Athenian admiral Chares, who killed every man and enslaved the women and children.
Alexander the Great himself crossed here and it was later controlled by Lysimachos.
Autophradates lay siege to Ariobarzanes in Assos. In exchange for Athenian support, Ariobarzanes gifts them Sestos.
Alexander the Great crosses from Sestos to Abydos. He then visits Troy and returns to Abydos. On his way, he sacrifices at the tomb of Achilles at Achilleion.