In ancient Greek times it lay on a land route for trade from the Black Sea to the Aegean and was a port for transporting the wood and fruit produced in eastern and central Thrace.

[3] The mythical and eponymous founder of the ancient Greek city of Ainos/Aenus was said to be Aeneus, a son of the god Apollo and father of Cyzicus.

[6] A surer sign of its antiquity comes from the Iliad, where Homer mentions that Peirous, who led Troy's Thracian allies, came from Aenus.

[9] As a subject ally of Athens, Aenus provided peltasts at the Battle of Sphacteria in 425 BC and sent forces to the Sicilian Expedition in 415.

[10] In 1091, in the nearby hamlet of Lebounion, Emperor Alexios I Komnenos (r. 1081–1118) and his Cuman allies dealt a crushing defeat on the Pechenegs.

[10] In 1237 a Cuman raid reached the city, and in 1294 it was besieged by the Bulgarians under Constantine Tikh and his Tatar allies until the Byzantines released Sultan Kaykawus II.

[10] In the ensuing civil war, Palaiologos signed a treaty with Venice here on 10 October 1352, securing financial assistance in exchange for ceding the island of Tenedos as collateral.

His admiral Limpidarios took over control of the city in his absence, despite the opposition of Nikephoros' wife Maria Kantakouzene (daughter of John VI).

The Gattilusi maintained their possession by exploiting the city's wealth, chiefly derived from salt pans and fisheries, and sending an annual tribute to the Ottomans.

Helena Notaras appealed to the Ottoman Sultan Mehmed II who attacked the city from land and sea and forced it to surrender in January 1456.

[12][13] In 1463 Ainos was given by Mehmed II to the deposed Despot of the Morea, Demetrios Palaiologos, as an appanage (along with parts of Thasos and Samothrace).

[12] The town gave its name to the Enos-Midia line, which briefly marked the border of the Ottoman Empire in Europe in the disastrous aftermath of the First Balkan War.

The border was shifted further northwest after the Turks made some limited gains in the Second Balkan War, recapturing the city of Edirne.

[16] The Has Yunus Bey Türbesi is a historic mosque and graveyard 300 m south of the castle which started life as a Byzantine chapel.

[17] The only historic monument in the resort area of Enez is the Sahil KervansarayI, the shell of an Ottoman caravanserai, which might have functioned as a customs office.

Local accounts suggest that it served a military function during the First World War, and it's therefore known as the İngiliz Kışlası ("English barracks").