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The centrepiece of Tartu is the Town Hall Square, built in classical style and shaped like a trapezoid. Throughout the history of the city, the square has represented its centre. It was originally a trade square that connected the hill fort with the harbour adjacent to the Emajõgi River. In this status, the town hall square existed for several centuries.

In the Middle Ages, the town hall, the centre of city administration, was built here. The town hall building that we can see now is the third one on this site. Despite the fact that Tartu is an ancient city, many buildings date back to the end of the 18th century. The reason for this is the famous Tartu fire, which destroyed almost the entire city centre in 1775. It was after this incident that the city was practically rebuilt and took on the look we see today.

Town Hall Square has had different names in different eras. Originally it was a market or fair square. When there were more markets in the city, Town Hall Square became known as the Big Market. During the German occupation there was Adolf Hitler Square, then Soviets Square, and since 1990 it became Town Hall Square.

During the last war almost all buildings on the south side of Town Hall Square were destroyed, including the Stone Bridge with its two triumphal arches. One of the arches was blown up in the summer of 1941 by the Red Army, and in 1944 the German troops finally destroyed the bridge during their retreat. In both cases, the natural water barrier delayed the advancing troops for some time.

Thanks to a Swedish period trial, it is known what buildings surrounded the square in the 17th century. In front of the town hall, they began to build the infamous execution pole, but one of the councillors was against the pole standing under his windows. His complaints reached the king. It was typical of medieval towns that buildings stood facing the square. This was also the layout of the Town Hall Square in Tartu.

One of the important symbols of the city is the Town Hall itself, located on the square, which was designed in 1789. To the right of the town hall, the row of houses on the north side of the square begins with house No. 2. On the corner, the dragon-headed gutter attracts attention. Such a decorative wrought iron detail can be found in different parts of the town. Another interesting detail is the rococo knocker garland around the window above the main portal on the side of the town hall. This house at No. 4 is home to the Dragon Restaurant and Hotel.

House number 6 on the corner of Rüütli Street houses a dental clinic and a jewellery shop. This house, which is the first building given to the university by Alexander I, was called the old university for a long time. Formerly, various offices were located here, classes were held, besides, many professors lived here.

House No. 8, designed like the Town Hall by architect Walter in 1781-1792, was home to famous Estonian artists, including landscape painter Konrad Mägi, who is commemorated by a plaque on the wall of the house. An art shop and a gallery remain here today.

The houses on Town Hall Square belonged to wealthy people. The most representative house is the 16th, which resembles a university building. Indeed, the house was built in 1797-1804 according to one of Krause's designs for the university. This building, acquired at the end of the 19th century, has 30 rooms, a large hall and commercial premises. Before the First World War, the house was rebuilt and completed. Throughout its history, the building has housed various clubs, a restaurant, cultural institutions, a bookshop, and a bank.

Tartu has its own "Leaning Tower of Pisa" - it is the leaning house No. 18, or Barclay's house, where the Field Marshal himself is known not to have lived, although a memorial plaque on the wall of the building states otherwise. This house, built at the beginning of the 19th century, was bought by Princess Barclay after her husband's death. Since Tartu's houses were built on the peat soil of the river valley, it is now necessary to reinforce most of the foundations. Barclay's building has sagged for this reason, and although the slope of the house has been preserved, the floors and streams inside the building have been levelled. This house houses a branch of the Tartu Art Museum with a permanent exhibition of contemporary Estonian art, and temporary exhibitions are also organised.

During World War II, the southern part of Town Hall Square was burnt down. It was rebuilt again using the ruins. Only the house at No. 3 has been rebuilt in its former form, although 1 extra storey has been added. The building used to belong to the Levenstern family. It was used to welcome and treat passing heads of state and other important people, now the building is at the disposal of the city government.

The fountain, which is located on the square in front of the town hall, was built in the post-war years. But not so long ago it was rebuilt and supplemented with a sculpture depicting students kissing under an umbrella. It was made by the master Mati Karmin. One day he took a photo of his nephew kissing a girl in the rain. This photo became the prototype of the sculpture.