The natural resources and the accommodating geographic position is the reason that Svilengrad has been inhabited since ancient times. Settlements on this territory trace back to the Stone age. A unique Thracian tomb was found near the village of Mezek in 411 BC. It is one of the most impressive beehive tombs of the Mycenaean type, preserved in its original state. Unique objects made of gold, bronze, iron, glass and pottery have been found in the tomb.

    There are many archaeological finds from the Roman epoch. Remains of the fortress on Hisariaka hill along with the monument Burdenis nearby can still be seen. During the late Roman age a great fortress called "Bukelon" was built near the village of Matochina. Today, only one tower stands rising up to a height of 20 m. In the Kaleto area near Mezek there is a medieval fortress from the 11th century, which had an important defensive role in that time. One of the greatest medieval battles in Bulgarian history took place here in 1205. Troops of Tsar Kaloyan defeated the then Latin army, lead by the emperor Baldwin.

    Near the villages of Matochina and Mihalich there are rock churches dating back to the 10th century. They are the best-preserved churches in Bulgaria of that type. The rock church to the Southwest of the village of Matochina is hewn into a rock terrace in the "Aypando" area. Its architecture resembles that of the cross-shaped domed churches.