Drabescus was part of the Roman and Byzantine Empires along with the rest of Greece. The region was conquered by Ottoman Empire in 1371.
In the 19th century, the town became centre of the Sanjak of Drama. In 1912 during the First Balkan War, Drama was taken from the Ottomans by Bulgarian troops. Subsequently, in 1913 as a result of the Treaty of Bucharest, following the Second Balkan War, it was incorporated into Greece along with the rest of eastern Macedonia.
World War II
Drama was occupied by Bulgarian troops in the wake of the German invasion of Greece, from 1941 to 1944 during World War II.
On 29 September 1941, in response to local communist guerrilla attacks against the Bulgarians in the villages of Drama, the Bulgarian occupation forces applied harsh reprisals in Drama, Doxato and several villages like Choristi, Kyrgia, Koudounia and Prosotsani.
On 4 March 1943, after midnight, the Bulgarian military authorities rounded up the Jewish population across their zone of occupation in eastern Macedonia and Thrace. The 4,000-strong community, including 589 Jews from Drama, was carried by train into Bulgarian territory and assembled in the tobacco warehouses that were empty this time of year. From there, the Jews were taken by train to the extermination camp of Treblinka. No one of the 589 Jews from Drama came back.