Haskovo celebrated its 1000th anniversary in 1985. To mark the event, a new clock tower was erected in the centre of the town. In medieval times it was known for the nearby Uzundzhovo fair, famous in all of Bulgaria.
In the 9th century—during the First Bulgarian Empire—a fortress was built in Haskovo that soon was transformed into a town. The town was located at the centre of a sizable region between the Klokotnitsa, Harmanliyska, and Maritsa rivers.
In 1395 the Eski camii (the Old Mosque) was built as one of the first in the Balkans. It is interesting that its minaret is slightly inclined.
In 1782, the town was known as Marsa. Many speculate that the current name came from the Arabic word "has" (possession) and the Turkish word "köy" (village) (Hasköy). Several historians have ascertained that the Turkish word "has" has roots to the meaning "clean". Strengthening this argument further, the town was literally called "the clean town" during the Bulgarian Revival period. The Turkish "köy" was subsequently substituted with the Bulgarian (and common Slavic) placename suffix "-ovo".
Most Bulgarians began to re-settle in Haskovo at the beginning of the nineteenth century. At this time, the settlement was a trading centre for merchants from Edirne, Enos, and Istanbul. Slowly, the area acquired a strong reputation for producing cotton materials, silk fabrics, and carpets.
After the liberation in 1878 Haskovo became a centre of high-quality tobacco region. However, now there is no cigarette production in the region as the once big Tobacco company "BT Haskovo" was closed. Nowadays there are some enterprises producing food, machinery and fabric.
A 32-metre-high statue of the Mother of God and the Infant Jesus was erected on the Hill of Youth near Haskovo in 2003. The monument was inaugurated on 8 September on the occasion of the Nativity of Holy Virgin Mary, when the day of the town of Haskovo is celebrated. It entered the Guinness Book of Records as the highest monument to Our Lady in the world.
The town centre has recently been the subject of many investments and renovation.