Haskovo Province in the context of "Edirne Province"

The Battle of Klokotnitsa (Bulgarian: Битката при Клокотница, Bitkata pri Klokotnitsa) occurred on 9 March 1230 near the village of Klokotnitsa (today in Haskovo Province, Bulgaria) between the Second Bulgarian Empire and the Empire of Thessalonica. As a result, Bulgaria emerged once again as the most powerful state in South-Eastern Europe.

Dimitrovgrad (Bulgarian: Димитровград [diˈmitrovˌɡrat]) is a town in Haskovo Province, Bulgaria. It is along the Maritsa River in the Thrace region, close to the provincial capital, Haskovo. Dimitrovgrad is the administrative centre of Dimitrovgrad Municipality.

Founded in 1947, Dimitrovgrad is a planned city built by the People's Republic of Bulgaria following World War II. The recently established communist government designed the town as a socialist model city and a modern industrial center. Dimitrovgrad is named for the first communist dictator of Bulgaria, Georgi Dimitrov.

Svilengrad (Bulgarian: Свиленград; Greek: Σβίλενγκραντ; Ottoman Turkish: Cisr-i Mustafapaşa) is a town in Haskovo Province, south-central Bulgaria, situated at the tripoint of Bulgaria, Turkey, and Greece. It is the administrative centre of the homonymous Svilengrad Municipality.

Mandritsa (Bulgarian: Мандрица, "Small dairy"; Albanian: Mandricë) is a village in southernmost Bulgaria, part of Ivaylovgrad municipality, Haskovo Province. It is known as the only Albanian village in Bulgaria. As of 14 December 2006, Mandritsa has a population of 75. It lies at 41°23′N 26°8′E / 41.383°N 26.133°E / 41.383; 26.133, 93 m above sea level.

Mandritsa is located on the right bank of the Byala Reka in the easternmost Rhodope Mountains, 15 km south of Ivaylovgrad and 2 km west of the Luda reka, which forms the border with Greece.

Haskovo (Bulgarian: Хасково [ˈxaskovo]) is a city in the region of Northern Thrace in southern Bulgaria and the administrative centre of the Haskovo Province, not far from the borders with Greece and Turkey. According to Operative Program Regional Development of Bulgaria, the urban area of Haskovo is the seventh largest in Bulgaria and has a population of 184,731 inhabitants. Haskovo has a population of 64,564 as of 2022, making it Bulgaria's 12th largest city.

The first settlement found in Haskovo is from circa 5000 BC. Haskovo celebrated its 1,000th anniversary as a town in 1985. To mark the event, a new clock tower was erected in the centre of the town.

Dimitrovgrad Municipality (Bulgarian: Община Димитровград) is a municipality in Haskovo Province, Bulgaria. The administrative centre is Dimitrovgrad.

Svilengrad Municipality is a municipality in Haskovo Province, Bulgaria. The administrative centre is Svilengrad.

Ivaylovgrad (Bulgarian: Ивайловград, "city of Ivaylo", Greek: Ορτάκιοϊ, Turkish :Ortaköy, "Middle Village") is a town in Haskovo Province in the south of Bulgaria set near the river Arda in the easternmost part of the Rhodope Mountains, and is the administrative centre of the homonymous Ivaylovgrad Municipality. The border with Evros, Greece is around two miles from the town centre.