The first part of Cieszyn to be inhabited was the Castle Hill. The town itself grew from the foot of the castle, initially on the facing hillside, developing along two parallel streets; ul. Polska (also called Tiefegasse ul. Głęboka) and Deutschegasse ul. Niemiecka (currently ul. Mennicza). At first the town centre was located at the site of the present Plac Teatralny, with the parish church of St. Mary Magdalene, the town’s school and the mint of the Cieszyn Princes all concentrated around this point. Stary Targ (the Old Market), which lies a little way above Plac Teatralny, was known for a time as Plac Maryjny (St. Mary’s Square) in the 19th century because of the Gothic statue of the Madonna and Child which was moved to this location from below the castle. In 2000 during its conservation 30 layers of paint were removed to reveal an authentic sculpture from the workshop of the famous Peter Parler, an architect and sculptor who worked for Emperor Charles IV in Prague. The discovery of the Cieszyn Madonna is one of the greatest revelations in the field of sculpture in recent years. Stary Targ is still a market place. 
      During the Middle Ages the town was surrounded by an embankment and a wooden palisade alongside the rivers Olza and Bobrówka and from the south-east by ramparts and a moat. The Dominican monastery founded in the second half of the 13th century was one of the buildings located beyond the town boundaries. In the 15th century a market place was established outside the embankments which Prince Kazimierz II donated to the town in 1496 along with two buildings with the aim of creating a new town square and town hall. At the beginning of the 16th century Cieszyn was surrounded by a wall with three gates; the Water Gate, the Freistadt Gate, both below the castle, and the Upper Gate on the opposite side of the town.
      The plan of old Cieszyn resembled the shape of a pear, whose borders on three sides were determined by natural features; the Castle Hill and two rivers; the Olza and the Bobrówka. In 1526 only 183 houses inhabited by something over 1000 people were located within the town boundaries. The land within the walls, which today constitutes the centre of Cieszyn, fell within the jurisdiction of the Town Council and the Executive Council. 
       Suburbs began to grow up beyond the town walls, of which Nowe Miasto (the New Town) was founded in the first half of the 16th century on the site of the former Dominican gardens. Górne Przedmieście (the upper suburb) grew up beyond the Upper Gate, belonging to Cieszyn, though for some time possessing its own judicial authority. Close to the castle were the suburbs of Frysztackie Przedmieście, Mała Łąka and Wielka Łąka and on the left bank of the Olza, the suburbs of Kamieniec and Brandys. All of these suburbs fell under the jurisdiction of the Cieszyn Princes and after 1653 the Teschener Kammer. What Cieszyn looked like in the 17th century can be seen in old pictures. After 1709 the Church of Jesus became the most imposing building in Cieszyn, built by the “grace” of the emperor on the hillside above the town, since as a Lutheran church it was not allowed to be built within the town walls.
      Over the centuries Cieszyn was visited by many natural disasters, including plagues and fires which destroyed the townspeople’s mainly wooden houses (e.g. in 1552 and 1720). After the great fire of 1789, when the whole town burnt down with the exception of ul. Nowe Miasto, significant changes occurred in the town. Some narrow streets were widened, the Dominican church became the parish church, and barracks were built on the site of the former parish church. The town walls were demolished, opening the way to the further development of the town. The Upper Gate was destroyed and its name – Wyższa Brama – given to the street linking the town with Górne Przedmieście. Górny Rynek (upper town square) grew up at the end of the 18th century between Górne Przedmieście and the town, initially as place for the trading of cattle from Galicia and later timber (from which it gets its locally popular name of Drewniany Rynek – the Timber Square). After 1876 the dominant feature of the square became the convent of the Sisters of Mercy of St. Charles Borromeo who came to Cieszyn from Trzebnica. The nuns organised ran many educational institutions for children and young women in the convent. At the turn of the 19th century Prince Albert von Saschen-Teschen founded the weavers’ quarter of Młynówka close to the river Olza in order to stimulate the growth of weaving in Cieszyn, which now, as Cieszyn Venice, is one of the most picturesque parts of the town. With the Prince’s help the suburb on the left bank of the Olza, named Sachsensberg after him, began to develop. He also gave his name to the avenue called today Masarykove sady which begins by the Friendship Bridge and goes towards Park Grabina.
      Cieszyn enjoyed its heyday at the turn of the 20th century when the town was transformed into a modern urban centre. Two mayors of that time, Jan and Leonhard Demel contributed most to this process. The town square was named after the first and the second gave his name to the so-called Demel Dungeon (Loch Demla) the pedestrian subway passing below the railway lines in Český Těąín. During their terms of offices the town acquired a modern urban infrastructure, the Town Hall its final appearance, and many new buildings were constructed; including the luxurious Imperial Baths. Large new barracks were built on Matterówka and named after Archduke Frederick. Additional storeys were added to the typically two-storey buildings in the town particularly around the Town Square and main streets and decorated in the style of the Viennese Art Nouveau. The townspeople of Cieszyn imitated Vienna in practically everything, proudly calling their town Little Vienna. Ul. Głeboka remained the main artery and the main shopping street, where the best known shops, restaurants and cafés were located. The streets further out from the centre such as ul. Garncarska, ul. Bobrecka, ul. Śrutarska, ul. Górna or ul. Ciężarowa – now ul. Michejdy, where the production and sale of furniture was concentrated, were considerably less attractive. The situation was similar with narrow side streets like ul. Schodowa located at the point of a passage in the old town walls, or ul. Bóżnicza where the Jewish synagogue was built in 1838 and enlarged in 1878. Streets in the suburbs e.g. ul. Frysztacka or ul. Hażlaska retained their rural character.
      The nationalistic and political leanings of the inhabitants of Cieszyn were also reflected in the town’s topography, which led to bitter political conflicts, at the turn of the 20th century. In 1898 a building on ul. Głęboka was given the name Deutsches Haus, and became the base for the various German associations operating in Cieszyn. In 1901 a building on the Town Square, which since the 17th century had been the tavern and inn Pod czarnym Orłem, was rechristened Dom Narodowy (the National House) by Polish nationalist activists. The townspeople’s differences could also be seen in the subject matter of monuments; Emperor Joseph II in 1884, Schubert in 1901, Schiller in 1906, Emperor Franz Joseph I in 1908, pastor Theodor Haase in 1912. After the division of the town in Cieszyn there were monuments to the Prince of Cieszyn, Mesco I in 1931 and the Legionists in 1934, while in Český Těąín to the First World War Dead in 1930 and to Jiří Třanovský in 1937.
      In 1891 an iron truss-bridge was built on the site of the main bridge below the castle where a bridge has stood since the Middle Ages. Its present name is the Bridge of Friendship, but it used to be known as the Long Bridge, Castle Bridge or Salt Bridge. In 1903, another bridge, the Most Jubileuszowy - the Jubilee Bridge (presently called Most Wolności – the Bridge of Freedom), was built. The architect and builder Ludwik Kametz built a wooden foot bridge between the two main bridges. The bridges linked the town centre with the districts of Cieszyn on the left bank of the Olza, where approximately 40% of the population already lived before the First World War. The Cieszyn section of the Bohumin and Koąice railway was built in 1869 and the railway station was opened in 1871. Owing to the rail connection industrial works began to spring up on the left bank of the Olza, such as the J. und J. Kohn (later Mundus) bent wood furniture factory, the Prochaskas’ and Kutzeras’ printing works and Jan Górniak’s brickworks. In 1911 a tramway connected the centre of Cieszyn with the railway station. Also built in this part of Cieszyn in 1882 was the shooting gallery of the Cieszyn Rifle Club (in existence since 1795) and the municipal gasworks.
      The division in 1920 of a town which had existed for centuries as one, had a great impact on both the Polish and Czech parts. In the Polish part of Cieszyn, where almost all public utilities were located, little changed. Apart from the health centre on ul. Bielska, no large buildings were put up, but the road system outside the town was gradually developed. It was a long time before the town’s infrastructure became independent of the Czech half of the town. The former halt by the Bobrówka became a station, the former residence of the Demels became the new location for the Town Museum by Park Pokoju, gathering all Cieszyn’s existing museum collections in one place. In 1922 the village of Błogocice, which had been closely linked to Cieszyn for centuries was incorporated into the town, and ten years after the village of Bobrek also became part of Cieszyn.
      The part of the town on the left bank of the Olza, conceded to Czechoslovakia, underwent considerably greater changes, transforming into a new town; Český Těąín. In a period of over ten years all the essential public utilities were established and large numbers of houses, most of them in good modernist style. State administrative and local government department buildings were built, also a cemetery, a fire station and a hospital. Schools and nurseries, including German and Polish ones, were not forgotten either. Three Lutheran churches were built in addition to the Catholic church in the Aleje, along with a synagogue and three Jewish houses of prayer. A Town Hall was built in 1929 and a new Town Square founded in front of it in 1933. Many tenement houses were built and a residential district sprang up in Rozvoj. Several factories were built in the town, with construction firms prospering best; in 1930 there were 20 of them, of which the best known belonged to Eugen Fulda and Karl Friedrich. Numerous shops, cafés and restaurants were established, and from 1933 onwards social life revolved around the café Avion, built onto the Hotel National, located next to the bridge below the castle.
      Many changes took place in the built environment of both parts of Cieszyn after 1945. The land area occupied by Cieszyn was increased following the incorporation of several of the surrounding villages, a similar process taking place in Český Těąín. Several large factories were built in the suburbs and on the outskirts of the town a number of large housing estates were built. The Communist authorities, in their urge to encourage the growth of heavy industry for ideological reasons, did not concern themselves overly with historic architecture, therefore some buildings were demolished to serve the needs of road traffic. Greater changes took place in Český Těąín where a bus station was built on the site of the Kohns’ furniture factory. In the town centre open spaces were developed, for example by the Town Square, sometimes with little thought as to whether the new buildings would suit the existing architecture. A new cultural centre and theatre were built in 1961. Most of the buildings that went up at this time were inspired by socialist realism. The importance of border crossings increased both for Poland and Czechoslovakia, so they were enlarged and improved on both sides of the border, until a new border crossing was built in Boguszowice, just outside Cieszyn.
      In the 1990s the authorities of both towns started to focus on and invest in improving the aesthetic appearance of their towns. Many old and historic buildings were restored, making use of new, more durable materials, for example the Bludowskis’ mansion, the former mint, which had an extension built on as part of the Cieszyn Historical Library.