Svilengrad is located ESE of Sofia and Plovdiv, South of Varna and Burgas, West of Edirne and North of the nearest Greek community Ormenio and Alexandroupolis in Greece.

The favorable natural conditions in the Svilengrad region and its strategic geographical location are the reason why it has been inhabited since ancient times.

Anastas Razboynikov's observations were confirmed in 2003-2004 during the rescue excavations along the route of the Trakia Motorway on the hill above the Kanaklia neighborhood, where a pit sanctuary from the Iron Age was discovered.

Under Khan Krum (803-814), Bulgarian troops often ravaged areas of the Byzantine Empire, according to the triumphal columns of Pliska for the conquest of the fortresses of Scutarion (now Shtit), Provat and others.

In 1205, Kaloyan's troops inflicted the first major defeat on the hitherto invincible army of the [[Latin Em[ire]], led by Emperor Baldwin.

In 1433, the Burgundian pilgrim Bertrand de la Broquierre passed through here, then the first armor bearer of Philip the Good, Duke of Burgundy, who traveled to the Holy Sepulcher and back to explore the possibilities of a new crusade.

Brokier describes how on the first day of the journey from Adrianople up the Maritsa River he and his comrades, numbering 10 horses, were transported in such a raft on March 12, 1433.

On the way to Constantinople, famous Bulgarian revolutionaries, educators and revivalists - Georgi Rakovski, Petko Slaveykov, Hristo G. Danov, Dragan Tsankov, Konstantin Velichkov - passed and stayed here.

During World War II, in 1940, one of the escape routes of Poles from occupied Poland led through Svilengrad to territory of Polish-allied France, where the Polish Army was reconstituted to continue the fight against Germany (see also Bulgaria–Poland relations).

[4] Svilengrad Peninsula on Davis Coast, Antarctica is named after the town, in connection with its pioneering role in the world aerial warfare history.