Asenovgrad ( ) is a town in central southern Bulgaria, part of Plovdiv Province. It is the largest town in Bulgaria that is not a province center. Previously known as Stanimaka (Станимака; ), it was renamed in 1934 after the 13th-century tsar Ivan Asen II.
Asenovgrad also includes the districts of Gorni Voden and Dolni Voden, which until 1986 were separate villages. According to the census data of 2021, the population of the city is 47 815 people. Above the town are the remains of the Asen Fortress, an old fortress that was strengthened under Tsar Ivan Asen II and turned into an important military post in the defense of the southern borders of the Second Bulgarian Kingdom.The city is known for its many churches, monasteries and chapels and is often called Little Jerusalem. It is also known as the "City of Bridal Gowns" because of the large number of ateliers and shops for wedding dresses and accessories.
The majority of Asenovgrad residents are Bulgarians, with representatives of the Turkish and Romani people ethnic groups in the city.
During the wars between the Bulgarian Empire and the Byzantine Empire, the city became a major military stronghold for the Bulgarian rulers. Due to aggravation of the relationships with the Latin Empire, in 1230 Bulgarian Tsar Ivan Asen II strengthened the local fortress Stanimaka and for this reason the city was named after him in 1934 (literally city of Asen). After Bulgaria was conquered by the Ottoman Empire, Romani people and Turkish people settled in Stanimaka, and nowadays make up 15% of the municipality of Asenovgrad's population, the rest 75% being ethnic Bulgarians and 10% – unknown and others.
The town was also inhabited by Greeks (52% in 1900) up to the post-World War I population exchanges between Bulgaria and Greece. Bulgarians from various regions in Greece settled in Asenovgrad, while its Greek inhabitants went to Naousa and Kilkis in Macedonia. Naousa and Kilkis are currently sister towns of Asenovgrad.
Tane Nikolov, revolutionary and leader of the Internal Macedonian Revolutionary Organization, spent his last years in Asenovgrad and died here in 1947.
Outside of the town is the 40 Springs () hunting and fishing resort. The climate is very pleasant during the winter and cool in the summer, which made the city and its surroundings very attractive for tourism. The southeast portions of the city are noted for tourist destinations and their urban development, including Parakolovo () and the 40 Springs complex.
In the late twentieth century the town was known for one of the first Bulgarian discos, Jumbare (), with 600 seats and a round dancing floor, it was completed in 1977 and was located in the Asenovec () hotel complex, which is full recovering, but the disco no longer exists.
The fortress is among the top 100 National tourist sights of Bulgaria and it is open during the entire year to visitors. Thousands of people and tourist walk to the top daily to take photographs, to relax and to see the beautiful view.
The town is famous for its numerous shops for wedding dresses and many Bulgarians come here in order to prepare for their wedding ceremonies.
Due to its specific geographical location the residents of the town enjoy a breeze called вечерник (literally "evening wind").
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