The name of town means Silk town because of the strong silk industry that had been developed here until the early twentieth century. Now the major businesses in the area are the wine industry and gambling (since it is illegal in Turkey and highly restricted in Greece, more than 10 local casinos attract gamblers from the neighboring countries).

The number of tells shows that the first permanent inhabitants of the area were the Neolithic farmers coming from Asia Minor in the seventh-sixth millennia BC. Thracians had their settlement here in the first millennium BC, which probably merged in the Roman station of Bourdenis on the Via Militaris Road in the second century AD. There is no certain evidence for the existence of a settlement in this place in the Middle Ages. The modern town emerged on both sides of a bridge over the Maritsa river that was built in 1529 by order of Mustafa Pasha (an Ottoman general). The town got his name and kept it until the end of the Ottoman rule in 1912, when the Bulgarian army liberated the town during the first Balkan war. During the Second Balkan war in 1913 the Ottoman troops devastated Svilengrad, massacring most of its population. Only a few buildings (among them are the Church of Holy Trinity (1834) and the Church of St. Demetrius (1898) survived this apocalypse. Nowadays the small border town hosts a lot of casinos and it is used as a starting point for various wine-tasting, birdwatching, mountain biking and cultural sightseeing tours in the area.

The village of MEZEK (200 inhabitants) is 12 km away from Svilengrad. It lies at the foot of the eastern Rhodopе mountains, just next to the Bulgaria–Greece border and not far from the Bulgaria–Turkey border. Mezek is famous for the preserved medieval fortress (Neut(e)zikon) and its ancient Thracian beehive tombs. The village is also well-known for its wineries and wine brands. Here starts the 450 km-long mountain biking track across the Rhodope mountains.