Chirpan is considered an heir to the Roman settlement Sherampol which was established close to the Roman town of Pizus (7 km north from today’s Chirpan). It has been accepted that Sherampol was established by fleeing refugees. According to historical documents the town came into existence on its today’s place in the XVth century. The present name Chirpan is supposed to be derived and adapted from the Roman name. It is connected with the Tekir well, around which the town was established. During the period of the Bulgarian Renaissance (the 18th – 19th century) the settlement had a town-type of structure with well developed agriculture and crafts.
The house-museum of the eminent Bulgarian poet Peyo Javorov is of special interest in the town. It is situated in the central town part. It is open all year round and preserves documents, photos and items that illustrate the Javorov’s work and life. The History Museum is situated in a 2-storey building. It conducts historical, archeological and ethnographic studies in the region of Chirpan. The house of G. Danchov, situated in the centre (now an entertainment establishment offering Bulgarian dishes) is a supreme example of the Bulgarian Renaissance Art. Tiankov's House that hosts the town art gallery and Manchev's House that hosts an art gallery, stand out with their exceptional architectural design of the past century. The most interesting and best-preserved house from the beginning of the 20th century now hosts a bank office. Holy Mother Church, built in 1846 is one of the 4 oldest churches of its kind in the town. The other churches are: St. Archangel Michael, St. St. Kiril and Methodius, and St. Spas.
Every year, Chirpan celebrates the "January Days of Javorov" – a festival of literature and art in honor of the great poet. Every odd year the town witnesses the "National Contest for Country Music Performers – Atanaska Todorova" in memory of the great Chirpan-born singer. On the 6th of September people celebrate the feast of the town.
Chirpan is located on the major motorway and railway line Sofia-Plovdiv-Bourgas and maintains regular bus connection with Plovdiv, Stara Zagora, Dimitrovgrad, Haskovo and other towns and settlements in the district and country.
The spa resort of Merichleri is located 17 km east from Chirpan. Its mineral water is excellent for curing intestinal diseases of many kinds. The architectural site of Karasura is situated 6 km north-east from the town. In the village of Granit, 20 km from Chirpan, you can see the oldest tree (1600 years) in Bulgaria – Granitski oak. The natural phenomenon of "Kamennata Satba" (The Stone wedding) is situated 25 km northeast from the town.