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The town is situated on the Haskovska River, in the Haskovo Highlands. Its southern sections are part of the low spurs of the Eastern Rhodope Mountains.
According to the archeologists, a settlement existed on the site of today's town as early as 7000 years ago, during the Neolithic Age. Numerous traces of habitation have been discovered from prehistoric, Thracian-Roman, late Antiquity and medieval times within the territory of the town and outside of it. In the 9th century, a fortress was built in Haskovo, which subsequently became a town during the First Bulgarian Kingdom - the centre of an important region between the Klokotnitsa, Harmanliyska and Maritsa rivers. Excavations and their study have provided much data about the history of Haskovo. In 1782, the town was mentioned in documents under the name of Marsa. The name by which it was widely known during the Ottoman period is Haskyoy (has - tur. clean and kyoy - tur. village). The settlement was also mentioned as Chistgrad (clean town) during the National Revival era. The mass movement of Bulgarians to live in Haskovo had already begun by the beginning of the 19th century. At that time the town maintained a lively trade with Odrin, Enos and Tsarigrad (Istanbul). It became famous for its cotton and silk fabrics and rugs. After the liberation of Haskovo from Ottoman rule at the beginning of 1878. the town's administrative, social and economic restructuring began. Mills, creameries, silk thread spinning workshops, and numerous tobacco warehouses appeared. New churches, schools, residential and administrative buildings were constructed. The beginning of the new, modern development of the town was set.

• Art Gallery.
• Literature Museum.
• Drama and puppet theaters.
• Paskaleva House, converted into an ethnographic museum.
• Shishmanova House, where an exibition of local crafts is situated.
• Gurkova House, currently the Composers' Home.
• Monuments to the famous Bulgarian revolutionary, Petko Voyvoda, and to the unknown soldier.
• Churches: Sts. Archangels Michael and Gabriel's (1861) with precious murals and an especially beautiful iconostasis and the Holy Virgin's (1837).
• Kirkovo School (19th century).
• Remains of the medieval fortress of Hisarya 7 km (4.5 miles) from Haskovo and 2 km (1.5 miles) from the village of Klokotnitsa. where, in 1230, Tsar Ivan Asen II won a crushing victory over Byzantium, who had violated the peace treaty with the Bulgarians. The battle of Klokotnitsa had important repercussions in Bulgarian history.
• The picturesque locale of Kenana (2 km or 1.5 miles from the town) - a beautiful oak forest with a spacious natural park, restaurants, tennis courts, and holiday centres.
• Haskovski Mineralni Bani (Haskovo Mineral Baths) 15 km (10 miles) west of the town - a balneological resort of national significance. The water from the 12 springs is with a temperature of the 48.5°C (119°F), and a capatcity of- 35 l/sec. (9 US Gallons/sec.). It is used in for treatment of diseases of the gynecological and skeletal-muscular system among others. It includes an open-air mineral water pool.
• Sharapanite - Thracian wineries from the 1st millenium B.C., approximately one hour's walk from the baths.
• The Izvorat na Belonogata (the Whitefooled Maiden s Spring) Tourist Complex 33 km (20 miles) from Haskovo. near Harmanli. The name comes from a poem by the National-Revival poet, Petko Rachov Slaveikov, which recreates the legend of a beautiful Bulgarian maiden, who rejected the splendor of the Ottoman palaces for the simple joys of home and the love of her beloved.

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