Simeonovgrad is one of the oldest settlements in Bulgaria and the oldest town in the region of Haskovo. It has a history of eight thousand years - from the Stone Age to the present days. The favourable geographic position of the town and the mild climate have contributed greatly to its constant historical development.

The town is located on the two banks of the Maritza river, in a hilly area near the outflow of the Sazlijka river. The hills, afforested mainly with oak trees, stretch from the hillocks of Chirpan, to the North of the Maritza river, to the East Rhodopes, situated to the South of river. The Maritza river flows between them through a picturesque defile, in the east part of which the present town is situated.