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The city is situated in the western section of the Upper Thracian Lowlands, where the Chepelarska River flows down from the Rhodope Mountains.

An ancient Thracian settlement existed in this territory. More than 100 Thracian mounds have been discovered with many valuable finds during their excavations. The medieval settlement, Stanimahos, was made up of a strong fortress, which defended the road to the Aegean. Under this name, it is mentioned in the documents of the Bachkovski Monastery from 1093. Later chronicles mention it under the names of Stanimako, Estanimak, and Scribention. Its most popular name was Stanimaka. Tsar Ivan Asen II fortified the fortress in 1230, and defeated the Byzantines in the following year. Due to these facts, the town was gradually re-named to Asenovgrad (the city of Asen). During the Ottoman dominion Asenovgrad was a Vaklf sector (land declared a government-supervised religious trust fund) and the centre of a rich agricultural area. After the Liberation it fell into the economic sphere of the rapidly developing Plovdiv.

• Town Historical Museum.
• Ethnographic Exhibition of old-style home life, set up in an old National-Revival building from the 19th century.
• Paleontological Museum in the locale of Badelema, founded as a filial of the Bulgarian Academy of Sciences. It preserves skeletons and fossils - some of which are unique in Bulgaria.
• Museum of Wine-Making and Vine-Growing.
• Churches: St. John the Precursor's (13-14th century). St. George's (Ambelinski), St. Georgi's (Metoshki), the Holy Virgin's -the Annunciation, Holy Virgin's (Dalbokata), and St. Demetrius' with mural decorations of high artistic quality.
• Old National-Revival houses with rare architecture and beautiful carvings.
• Tsar Asen's Fortress - 2 km from Asenovgrad, towering over the very highway to Smolyan from a high cliff. The fortress has existed since the time of the Thracians, but took on strategic significance in the Middle Ages. After the battle near the village of Klokotnitsa (1230), when Tsar Ivan Asen II (the most successful Bulgarian ruler, under whom Bulgaria bordered on three seas), defeated the Epirian ruler, Theodore Angel Komninos, he fortified and expanded the fortress and marked his victory with an inscription, chiseled into the cliff above it. The fortress' church, The Holy Virgin of Petrich (12-13th century), relatively well preserved, including valuable murals, was restored twice. In 1991 it received the status of an active shrine.

Bachkovski Monastery of the Assumption of the Holy Virgin (11th century, still currently operated by monks). It is situated 11 km from Asenovgrad. It was built in 1083 by the Georgians Grigori and Abasiy Bakuriani in one of the possessions given to them by the Byzantine Emperor Alexius Komninos. After it was annexed to the Second Bulgarian Kingdom during the 13th century, it became a cradle of Bulgarian medieval spiritual culture. It especially flourished during the reign of Tsar Ivan Alexander - the sponsor-patron (founder) of the monastery. After the capital, Tarnovo, fell under Ottoman rule in 1393, St. Patriarch Evtimiy of Tarnovo was banished to Asenovgrad. Scholarly monks gathered around him and, thus, the traditions of the Turnovo School of scholars continued. The monastery's buildings form a large, closed, rectangular yard, where three churches are situated - St. Archangels' (12th century), the Holy Virgin's (17th century) and St. Nicholas'- which preserve a great wealth of murals. The most sacred item of the monastery is held in the Holy Virgin's Church - the miracle-working icon of the Holy Virgin from 1311. The architectural ensemble is complemented by the monastery's dining hall (17th century) - an unrepeatable gallery of iconic murals. The oldest building, dating from the founding of the monastery, is the ossuary with its valuable murals. The monastery museum preserves antique church objects, liturgical books, icons, decorations, church vessels, and a numismatic collection.

• Monasteries: St. Petka's , Sts. Kirik and Yulita's, St. Nedelya's (Arapovski), and Kuklenski.
• Eneolit (Late Stone) Age religious centre in the village of Dolnoslav.
• Thracian rock sanctuaries. A unique, silver ritual plate from Hercules was discovered in one of them.
• Chervenata Stena (The Red Wall) Biospheric reserve 9 km from the city; over 600 species of higher plants thrive here.
• 40 karst lakes near the village of Gornoslav.

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