The modern town is the successor of the Ancient Roman settlement of Sherampol and re-emerged in the beginning of the 15th century, its current name likely being derived from the Roman one. There has been extensive archaeological excavation at the Karasura (Carasura) site. During the Ottoman rule of Bulgaria, Chirpan (Turkish: �?rpan) was known for its craftsmen and agriculture. The town suffered badly from an earthquake on 18 April 1928.
Chirpan was the birthplace of Ottoman Turkish soldier Abd�lkerim Nadir Pasha, and the Bulgarian poet Peyo Yavorov, whose native house is now a museum. Chirpan was the home of painter George Danchov. His house in the centre of the town is an excellent example of Bulgarian National Revival architecture