For several centuries, the main street of Plovdiv started from the only bridge over the Maritsa River at the time and reached Dzhumaya Sqare. It was called Uzun charshiya, which means long street. Here was the center of economic life in Plovdiv for several centuries. Evliya Chelebi wrote in the 17th century that the street was covered with large stones in ancient times, and there were 880 shops along it. The massive buildings on both sides of the street were hidden by one-story and two-story shops. They narrowed the otherwise wide street so much that two carts could barely pass it.
The situation on Dzhumaya Square was similar. Opposite the mosque stood barracks tilted to one side, with barely fitting shutters on the openings. They sold charcoal and kindling wood. The smell of mekitsi, simid, milinki and other delicacies wafted in the northeast corner of the square. It smelled of coffee in the southeast corner. The restaurant was known for its numerous fans of backgammon and a number of other games. On the opposite side was an Albanian inn, a boza shop, tobacco and trinket sellers. The only massive building was a wholesale manufactory. These barracks disappeared at the end of 1878, when the square was opened to its present size.
The first elected mayor of Plovdiv, Kostaki Peev, took office in 1878. He tried to pave at least the main street following the European example, but neither found masters for making the paving stones, nor did he have the funds. The only thing he managed to do was replace the broken stones with cobblestones. It was only in 1900 that attempts were made to pave the streets in Plovdiv. Naturally, the main street was the first. First, they laid the pavement in front of Kurshum Khan.
However, a real pavement of small syenite blocks, fan-shaped, was laid more than ten years later. To everyone's amazement, the first street with the new pavement was not the main one, but the one where Mayor Denyo Manev lived.
In the 90s of the XIX century the commercial street of the city crossed the Dzhumaya Square and gradually reached the Aladzha mosque opposite the building of today's Plovdiv municipality. This new street became known as Glavna Stantsionna because it led to the railway station. And here there were rows of barracks, which almost closed the road in some places. The first paving of this new part of the main street was laid in 1901. The pavement started from Dzhumaya Square and reached the current monument to Milyo.
In 1896 Plovdiv surpassed the other centers in the country, acquiring an urban plan. Josef Schnitter, the author of the plan, predicted that the central street of Plovdiv from the Tsar Simeon Garden to the Maritsa Bridge would be 50 meters wide. The specialist followed the European models, realizing that Plovdiv will grow and the main street will take more and more traffic in the future. When they found out about the project, the municipal councilors objected. Many of them had houses and shops that, according to Schnitter’s plan, were to be demolished. After long and painful disputes, it was decided that the street from the Maritsa Bridge to Dzhumaya Square would be 8 meters wide, and from there to Tsar Simeon’s Garden – 12 meters. Outraged, Josef Schnitter went to Sofia at his own expense, and after a long and continuous struggle, managed to make an agreement for 16 meters for Knyaz Alexander Street and 12 meters for Targovska Street (now Rayko Daskalov). Thus, the fate of the main street was predetermined in the late nineteenth century.
For a long time, Schnitter’s plan remained only a book. This was the case until 1922, when the mayor, Dr. Ivan Kesyakov, decided to act. This time, councilors backed the mayor, and in April their decision was confirmed by ministerial order. The beginning of the reconstruction was to begin on May 1, 1923. However, those affected hurried to block the decision. Delegations went to the district governor and the cabinets. An order came from Sofia to stop the reconstruction. Moreover, on May 1, the entire main street was blocked by troops and police. And with a little trick the first house was demolished, and two or three days later also the next and slowly the affected owners reconciled and began to demolish their buildings themselves.
The main street of Plovdiv has acquired a European look for the first time in centuries. Construction unseen before started. Wide sidewalks appeared. In the 1930s, municipal transport buses set off on it, and trolleybuses took their route 20 years later. However, the mistake of the previous rulers turned out to be fatal - the main street turned out to be too narrow to take the traffic. Otets Paisii Street was opened as an auxiliary, but even that didn’t help. That is why in 1936 they started talking of drilling a tunnel under the rocks of the Three Hills to solve the city's transport problems. This didn’t happen until 1961.