In and around Haskovo, evidence has been preserved that confirms its long history during the prehistoric, Thracian, Greek, Roman, and Byzantine periods.

The village acquired a largely agricultural character during most of the Ottoman period; there was also a thriving cottage industry and craftsmen such as saddlers, tanners, shoemakers, furriers and soapmakers, dyers, and chandlers made their home in Hasköy.

In 1592, the Ottoman Grand Vizier Sinan Pasha commissioned the building of two caravanserais, two baths, shops, a mosque and an almshouse at the request of the people.

According to the Austrian historian and orientalist Joseph von Hammer-Purgstall, Sinan Pasha also inaugurated the nearby Uzuncaova (Uzundzhovo) fair, which would become famous in all of Ottoman Bulgaria.

In the 1870s Hasköy was a hotbed of revolutionary activity during the Bulgarian National Revival and subsequent Russo-Turkish War of 1877-1878, after which de facto Ottoman control of the town came to an end.

Haskovo was part of Eastern Rumelia from 1878–1885, and was then incorporated into the autonomous Principality of Bulgaria, which declared full independence from the Ottoman Empire in 1908.

The most notable cultural landmarks in Haskovo are the Ivan Dimov drama theater, renovated in 2004, the Museum of History, and an art gallery.

The annual Colourful Thrace Sings and Dances folk festival takes place in the nearby park Kenana.

Municipal landmarks include the Thracian Aleksandrovo tomb as well as Uzundzhovo's Church of the Assumption, built originally as a mosque during Ottoman times.

The historical features and the rich culture of the region, in combination with the well-developed transport and tourist infrastructure, are a favorable factor for the development of tourism.

The partnership relations established by the municipality with cities from England, Austria, France, Greece, Turkey, Italy, Spain, Portugal, the US, Russia, Serbia, Belarus also have a valuable contribution in this respect.