The earliest settlements on the territory of the city are dated back to the 6th millennium BC. There were several prehistoric settlements on this territory, but the oldest and most important one was located on hill known as Nebet tepe. Initially the village was situated in a naturally sheltered and consolidated place on the front side of the northern hill. It gradually expanded towards the other hills to become the most significant Thracian city on the territory of Bulgaria. At that time the lands of today's Plovdiv were inhabited by the Thracian tribe Bessi. Around the three eastern hills the Thracians established the ancient settlement of Evmolpiass, which was later on called Pulpudeva. The scientists are still not sure if the name of the city at that time was Eumolpia or Pulpudeva. In the year 342 B.C. the town was conquered by Philip II of Macedonia and was called Philipopol - Philippoupolis - city of Phillip II of Macedon. That is the time when Kingdom of Macedon started to dominate as the most powerful force on the Balkan Peninsula, to reach its peak during the reign of Alexander III the Macedon. During the Roman times it was given the name of Trimontium (Town on three hills), while in Byzantine reign it was named Philippoupolis. The Via Militaris (or Via Diagonalis), the most important military road in the Balkans, passed through the city during Roman times, which was a period of growth and cultural excellence. The Slavs named it Plovdiv. In the Middle Ages, Plovdiv retained its strategic regional importance, changing hands between the Byzantine and Bulgarian Empires. Plovdiv came under the Ottoman rule in the 14th century. In 1878, Plovdiv was made the capital of the autonomous Ottoman region of Eastern Rumelia; in 1885, it became part of Bulgaria with the unification of that region and the Principality of Bulgaria.

Plovdiv is divided into two parts - the old town Stariyat grad, which occupies the three eastern hills, and the lower town spread in the plain below. The modern town of Plovdiv offers entertainment and vigorous sights, but the old town /conveys best/ carries the atmosphere and the culture of the city. The ancient Plovdiv part of the three-hill town is an architectural and historical reserve. The Ancient Plovdiv has preserved until nowadays the atmosphere of the Renaissance. The modern town of Plovdiv however is a trade and culture centre. Modern Plovdiv is a bunch of museums, churches, banks, hotels, cafes, restaurants, cinemas, shops, bars, bazaars, music clubs, casinos etc. Here rest the ruins of a Roman stadium and remnants of the Roman forum, here could be also seen several mosques and original Turkish baths. The most outstanding buildings in Philippopolis from the Roman period, the Amphitheater had richly decorated floors, usually with big mosaic compositions. Many mosaic floors of this kind have been found on the territory of the ancient town. The earliest mosaics date back to the 2nd c. but the findings of the 4th and 5th c. are the most numerous. Especially noteworthy is the floor decoration of a rich Philippopolis home that existed from the end of the 3rd till the end of the 5th c. Nearly 700 square meters of this remarkable building have been studied.

The modern centre of Plovdiv provides entertainment and rich cultural life. Classical concerts take place at the Plovdiv Philharmonic Orchestra's concert hall, where in January the Winter festival of Symphony Music is held. The Olovdiv Opera is located near the concert hall. The Mesalitinov Theater Plovdiv is the venue for classical drama, child shows, and modern theatre. The building of the Plovdiv TV and the Radio, and the biggest cinemas are situated in the modern city. In the Plovdiv Fair Camp different international exhibitions and expos are held all year round.

The old town embodies Plovdiv's long history – the Thracian fortification subsumed by Macedonian masonry, overlaid with the Byzantine walls and by great timber-framed mansions, painted in brick-colors, in yellow and beige, erected during the Bulgarian Renaissance, symbolically looking down upon the derelict Ottoman mosques and artisans' dwellings of the lower town. After the end of the 17th century, Plovdiv marked the beginning of its steady development as a major economic centre in the Ottoman Empire and around the mid-19th century it became the biggest city in the Bulgarian hinterland. The higher economic potential of the population led to the appearance of a new type of urban Plovdiv dwelling: the "Plovdiv city house". In the course of its development in the 18th and 19th centuries, it was characterised by two principal types: asymmetrical and symmetrical. The oldest preserved examples of Plovdiv houses are dated to the middle and to the end of the 18th century. These are buildings with asymmetrical plan, on two storeys and not very big. They have expressive facades, broken by bay windows jutting over the street, open porches in the floor and a veranda with wooden columns on the ground floor towards the courtyard. This early residential Plovdiv type has wooden ramshackle structure that was very characteristic of the period, built on a solid stone foundation. Plovdiv architecture style demonstrates the strong influence of the mountain-type houses built in the Balkan Range region and in the Rhodope Mountains from where the master-builders came. The requirements of life in the big city gradually necessitated glazing of the open porches. This is how the typical rooms for receiving guests appeared - hayets - whose ceilings are richly decorated with wood-carved compositions. Among the more remarkable monuments of the asymmetrical type of houses are the Fournadzhiev house, the house at 5a, Dr. Stoyan Chomakov Street, the Klianti house, etc. Plovdiv is not merely a parade of antiquities : the city's art festivals and trade fairs rival Sofia's and its restaurants and promenade are equal to those of the Bulgarian capital city.

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