Places to visit

Tallinn Old Town - The First Encounter


This is a relatively short and simple route that covers the most famous landmarks of the city. From the Viru Gates to the Town Hall Square, through the Pikk Jalg (Long Leg) street to the Upper Town, then descending to the Kiek in de Kök Tower and passing through the streets of the Old Town to the Northern Gates - the Fat Margaret Tower. Stories, legends, tales, beauty, and mysteries of the city.

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Evgeny Praisman (author)
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The Viru Gates have been preserved in Tallinn since the 15th century. They are one of the oldest structures in the city. It is said that the name "Tallinn" originates from "Taani linn," which means "Danish town" in Estonian. Indeed, the first significant settlement was established here by the Danes. The Livonian Chronicle mentions that a large Danish army, led by the legendary Valdemar II the Victorious, captured a small settlement of Estonians called Kolyvan. Valdemar's father was also named Valdemar, and his mother, Sophia, came from the Minsk-Polotsk branch of the Rurik dynasty.

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The Town Hall Square and the Town Hall itself are the city's heart. It was also built during the city's early development in the 14th century when the Danes sold their possessions in Tallinn to the Teutonic Order, confirming the city's rights and privileges and incorporating Tallinn into the Livonian holdings of the Teutonic Order. As a result, the Town Hall has nearly 600 years of history and is Europe's oldest fully preserved town hall. On its façade, you can see two drainpipes in the shape of dragon heads, and on the ground floor, there is a restaurant called "The Dragon," which is fully styled as a medieval tavern. To enhance the medieval atmosphere, they offer hand-drawn beer, servers dressed in appropriate attire, and the lighting is exclusively candlelit.

In the middle of the square, embedded in the cobblestones, is a large metal disc known as the "Zero Kilometer of Estonia." You will find the old pharmacy opposite the Town Hall, in the corner of the square. It has been located in the same building since 1422. Today, it serves as a museum.


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The Stone Tower of Tallinn, also known as the Tallinn Long Leg Tower, was constructed in the 17th century, likely replacing an earlier wooden tower that stood in its place. In 1380, Wilhelm von Freyhausen, a master of the Livonian Order and ruler of Estonia from 1364 to 1385, granted permission to construct stone gates. Around 1450, the tower underwent renovations, including expansion, adding at least two defensive floors, and installing a staircase passage. It is possible that an open defensive floor was also constructed, making the stone portion of the tower exceed 20 meters in height. In 1454, the magistrates paid the blacksmith Rosenberg for the gate's installation, and in 1455, blacksmith Klaus Denenilu for the production of two weather vanes. In 1608, the upper part of the tower was reconstructed. During the 19th century, the tower housed a military garrison. The residents of the lower town built the tower to protect the burghers from the abuses of the nobility and knights residing in the upper part of the town. The magistrates charged a high fee for passage through the gates in a carriage or wagon. Presently, the tower contains residential premises and studios.

Photo by By PIERRE ANDRE LECLERCQ - Own work, CC BY-SA 4.0

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As we ascend to the Upper Town, we enter a place that knights and rulers of the order once inhabited. The tower's gates were locked, dividing the Upper and Lower Towns. This more extended street was named Long Leg Street. Adjacent to it is another shorter street leading to the Lower Town through a tower. Due to the existence of "long leg" in Tallinn, the city is jokingly referred to as "limping" or "lame."

Photo By Roman Rozbroj - Own work, CC BY-SA 4.0

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We have reached Kiriku Square. Here stands the Dome Cathedral, which was built on the site of the city's first significant church dating back to Danish rule. The green-coloured building in the Neo-Renaissance style is known as the Knightly Assembly Building. Indeed, since medieval times, structures here were used as knightly halls. The building was constructed in the 18th century for the urban aristocracy, Estonian knighthood. During the Soviet era, it housed the city library.

Photo By giggel - Panoramio, CC BY 3.0

This is the most famous observation deck in the city. The most beautiful and recognizable photos of Talin are taken from this spot, where the Spiers of towers and bell towers of churches rise with tiled roofs.

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This part of the upper town became the residence of power during the reign of the Russian Empire. Russian authorities conceived and constructed the building, but funding was quickly halted. Finally, the construction was finished on his funds by an Estonian aristocrat of Swedish origin, Stiienbok. In the 18th century, the state institutions of the Russian Empire were located here. Today, it houses the government of the Republic of Estonia and the State Chancellery.

Photo by Ivar Leidus. Собственная работа, CC BY-SA 3.0

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They were first mentioned in 1233 in connection with events in a complaint to the Pope as the "Blood Bath," orchestrated by the Knights of the Teutonic Order, killing all Danes and piling their corpses at the church's altar. The church was founded in the early 13th century and consecrated in 1240 as the Roman Catholic Cathedral of Northern Estonia. It is likely that a school called the Cathedral School was opened at the church in the 13th century, first mentioned in 1319. The first reconstruction was done in the second half of the 13th century, and the building was converted into a basilica in the 14th century. The nave ceilings were finally completed in the early 15th century. Following the Reformation in 1561, it became a Lutheran cathedral. A fire in 1684 resulted in the loss of much of the building's decor and the tower over the central nave. In 1778-1779, the western tower was built in the Baroque style by architect K. L. Geist. In 1878, a modern organ crafted by F. Ladegast in Berlin was installed.

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The upper town did not remain without a Russian Orthodox cathedral, a symbol of power and endless Russian influence over the long years during which Estonia and Tallinn were part of the Russian Empire. The cathedral was built in 1900 in memory of the miraculous survival of Emperor Alexander III in a railway disaster on October 17, 1888. Out of eight proposed locations for the cathedral, the best place was the square in front of the governor's palace (now the parliament building). However, for ideological and political reasons, authorities planned to demolish the cathedral in 1928, during the first period of Estonian independence. The cathedral's active defender was Metropolitan Alexander (Paulus), head of the Estonian Apostolic Orthodox Church, who transferred his seat here from the Transfiguration Cathedral in 1936. At the end of 1936, the cathedral's rector became Archpriest N. Päts, the brother of the President of the Estonian Republic, K. Päts. The cathedral was closed during Estonia's time as part of the Reichskommissariat Ostland of the German Empire.

From here, a slope descends towards the fortress walls. The upper town is called Toompea in Estonian. Thus, many names in the upper village include this word. But when did the "Russian" period in Tallinn's history begin? We will learn about that later.

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The name Kiek in de Kök is an old (German) name for towers, primarily those that were part of city fortifications. They got their name from the fact that the tower's occupants could see what was being prepared in the kitchens of nearby houses. During the times of the Hanseatic League and the Teutonic Order, towers not only in modern Germany (for example, in Magdeburg) but also beyond, such as in Gdansk (Danzig) and here in Tallinn, were given this name. Over its existence, the tower managed to repel numerous attacks on Tallinn. The most severe damage was inflicted during the Livonian War when, in 1577, the troops of Ivan the Terrible besieged Tallinn. Cannonballs are still embedded in the tower walls as a reminder of those events. However, the Livonian War was only the beginning of Russian expansion. Peter the Great will complete the final victory over the Swedes, reach the Baltic Sea, and capture Estonia.

This place is called the courtyard of the Danish King, that very Valdemar who, in essence, founded what is today called Tallinn. According to legend, a flag descended straight from the heavens onto him here. It was red with a white cross - the flag of Denmark. On this occasion, Danes hold an annual commemorative ceremony here.

Photo By Taivo Pungas - Own work, CC BY-SA 4.0

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The Adamson-Eric Museum is one of the branches of the Art Museum of Estonia and is located in the Old Town of Tallinn. The museum is dedicated to the work and life of Adamson-Eric, a renowned Estonian artist known for his work in various artistic fields. He was a painter, a graphic artist, a textile designer, a ceramist, a metal artist, and a master of leather and furniture.

The museum's permanent collection features many Adamson-Eric works, including paintings, ceramics, leather, textiles, and jewellery. It provides a comprehensive overview of his artistic career, displaying his versatility and creativity.

The museum is housed in a beautiful, historic building, a cultural monument. The structure, dating from the 16th century, adds an atmospheric backdrop to the varied and colourful works of Adamson-Eric displayed inside.

Apart from showcasing Adamson-Eric's creations, the museum hosts various art and design-related temporary exhibitions, often focusing on modern and contemporary art. In addition, it has an educational program, providing lectures, workshops, and guided tours. It's an important cultural and educational hub for art enthusiasts in Estonia.

Adamson-Eric (1902-1968) worked in various techniques and forms of art, from painting to furniture design. His works exhibited in this ancient merchant building are magnificent canvases, painted porcelain motifs, original jewellery pieces, and other masterful creations.

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The Church of the Holy Spirit in Tallinn, Estonia, is an essential landmark due to its historical and cultural significance. This well-preserved medieval church stands out for its simple yet remarkable architecture, reflecting the Gothic style prevalent in the region during the 13th to 16th centuries.

Pastor G. Müller, who lived in the 16th century, is a notable figure associated with the church. Müller is remembered for his contribution to Estonian culture, particularly in language. He is recognized for having delivered sermons in Estonian, which was a significant step in acknowledging and establishing Estonian as a language of religious discourse.

Therefore, the church serves as a place of worship and is a testament to Estonia's cultural and linguistic development. Furthermore, its preserved state provides visitors with a unique opportunity to experience a piece of history that continues to influence Estonia's cultural identity.

In addition to Pastor G. Müller, the Church of the Holy Spirit is also associated with Baltasar Russow, the author of "The Chronicle of Livonia." This work provides a crucial historical account of life in the region during the 16th century.

One of the remarkable features of the church is the carved wooden clock on the exterior wall. The watch was installed during Swedish rule in 1684 and is the work of the renowned master craftsman Christian Ackermann.

Ackermann, originally from Königsberg, had worked in various cities, including Riga, Stockholm, and Gdańsk, before he moved to Tallinn in 1675. He established his sculpture workshop here, contributing significantly to the city's artistic scene.

Unfortunately, Ackermann's life in Tallinn ended tragically during the plague epidemic 1710. However, his legacy continues through his works like a clock at the Church of the Holy Spirit, a testament to his craftsmanship and an essential artefact of Tallinn's historical and cultural heritage.


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The Bourse Passage ("Börsi käik" in Estonian) in Tallinn is a historic alleyway known for its significance in trade and commerce. Nestled between buildings along Pikk Street, its most notable landmark is the Great Guild Hall to its north. The passage also features a unique outdoor exhibition called the "Stride of History." In addition, important dates commemorating significant moments in the country's history are inscribed on the paving stones of the sidewalk.

The alley was named "Bourse Passage" after the Exchange Committee, which used to hold meetings in the Great Guild Hall. Before 1939, it was known as the "Guild Alley." Its modern entrance from Pikk Street, marked by an arch gate, was built in 1413.

The Great Guild represented the merchants of the Lower Town and was a secular organization from the beginning. Therefore, unlike other guilds, it did not have a patron saint. Instead, it had its coat of arms and charter. This unique blend of trade history and architectural beauty makes the Bourse Passage a significant destination in Tallinn.


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The Rechmann House in Tallinn, built in 1910, is an exquisite example of Art Nouveau architecture. The building is ornately decorated with masks, floral motifs, and two unique figures: a man with binoculars peering down from the roof towards Pikk Street ("Long" in Estonian) and a black cat on the side facing Hobusepea Street ("Horse Head" in Estonian).

The man's figure dates back to a local legend from 300 years ago. It's said that a bachelor lived in the house that once stood on the site who had a notorious habit of peering through his window into the house across the street. In that house lived three young women, and the man enjoyed watching them as they prepared for bed. His wide-eyed figure on the roof, complete with a lustful half-smile, immortalizes his voyeuristic pastime.

The modern house, built at the beginning of the 20th century, was designed by a young architect named Jaak Rosenbaum. Rosenbaum had moved from Tartu to Tallinn in 1907 and soon received a commission from a wealthy local entrepreneur, Rechmann, to design a house on the corner of Pikk and Hobusepea Streets. In addition to the ornate decor, Rosenbaum decided to adorn the building with the bust of the voyeuristic man and a cat figure, possibly influenced by an amusing urban legend he'd heard. August Volz crafted the sculptures.

The figures soon gave rise to even more local legends. One suggests that the house owner used to take evening walks, leaving his young wife at home. He placed his figure on the roof to keep an eye on her while his resourceful wife installed a cat figure on the opposite side, implying she'd still escape if she wished to. This playful interaction between history, architecture, and local folklore highlights the unique charm of Tallinn's architectural heritage.

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The St. Canute's Guild in Tallinn was established around the 14th century. Initially, it was a spiritual fraternity which later transformed into a commercial association of German-origin master craftsmen and artisans. However, for a modern traveller, visiting the house occupied by this Guild can be pretty intriguing.

The current building that belonged to the Guild was rebuilt, combining three adjacent houses under a familiar facade. Each of these houses came from different times and epochs. Hence their combination makes for an exciting spectacle from a purely aesthetic perspective, not a historical understanding. The first house was acquired in 1326, the second in 1406, and the third in 1800.

It's worth taking a closer look at the remarkably curious facade. A strict design executed in neo-Gothic style dates back to the 19th century and is adorned with two giant statues. On the left, you'll find Saint Canute, the patron of the Guild and king of Norway, England, and Denmark. On the right is Martin Luther, a renowned and revered church reformer. You can also spot the coats of arms of Tallinn – with three lions and a white cross on a red background- and Estonia's Great and Small coats of arms on the portal.

Photo By Alma Pater - Own work, CC BY-SA 3.0

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The House of the Blackheads in Tallinn is a historical building that was once used by the Guild of St. Olaf (Oleviste gild), which united artisans considered to be of the lower class: butchers, tanners, gravediggers, and others. Mostly, these were ethnic Estonians, while in other professions, Germans dominated. The Guild used this house on Pikk Street for meetings as early as the 14th century. The building was significantly rebuilt in the 15th century. By the end of the 17th century, the St. Olaf's Guild ceased to exist, merging with the Canute Guild. In 1919, the Blackheads Brotherhood, located nearby, bought the house and connected the two buildings. As a result of numerous reconstructions, the facade of the building transformed from a medieval look into the fashionable Art Nouveau style of the time.

The Guild also had a military function, as their cavalry squad, serving until the age of fifty, was part of the city's militia. They gathered in their "headquarters" in the evenings, talked business, and drank beer. Twice a year, they accepted new members into the brotherhood. In 1671, six new members collectively presented a rather unusual gift - a silver cup. It had a secret: it had a double bottom, the upper one held by the pressure of poured wine, but as soon as the cup was tilted to drink it, a figure of a boy located under the upper bottom would flip the false bottom and all the wine would drain into a secret chamber, leaving the drinker with nothing.

In the late 16th century, Reval (as Tallinn was then known) was preparing to welcome King Sigismund III Vasa of Sweden and Poland. For the monarch's visit, the facade of the building was reconstructed from the Gothic style into the fashionable Renaissance style of the time, decorated with bas-reliefs depicting Jesus, and between the windows appeared knights. The inscriptions under them read: "Helf Godt Allezeid" (God always helps) and "Godt is mein hilf" (God is my helper). The house's door is also attractive with the head of St. Maurice and typical rose-shaped nails for those days.

Admiral Ferdinand Bellingshausen, the discoverer of Antarctica, was born in a German family on the now Estonian island of Saaremaa, was brought up in the naval cadet corps in St. Petersburg, and from 1833 to 1838 he lived in this house, serving as the commander of the fleet division. Unfortunately, during the restoration of the building in the early 1990s, his memorial plaque was removed and never reinstalled.


The House of the Burgomaster Hukk, also known as House of the Hukk, is a historic structure in the Old Town of Tallinn, Estonia. This structure dates back to the medieval period, and its architecture reflects the styles of the time. The House of the Burgomaster Hukk was the residence of a high-ranking official, the burgomaster, a title for a mayor or chief magistrate of a town in certain European countries.

Lai Street in Tallinn is remarkable due to two Linden trees growing in front of one of the houses, which is unusual because trees generally do not grow on other streets of the Old Town. There's a local legend associated with these trees.

It is said that during one of his visits to Reval (the historical name of Tallinn), Peter I of Russia typically would rent horses at the port and pay a visit to the burgomaster (mayor) to enjoy some coffee or beer. Unfortunately, during one of his visits, the house of the burgomaster, who was Johann Hukk at the time, was undergoing renovations. Because of this, it was impossible to host the Emperor in the house, so Hukk set up a small table for him right on the porch.

It was a hot day, and the coffee was warm, which led the displeased Peter to comment that it wouldn't be a bad idea to plant a couple of trees in front of the house to provide some shade. Hukk replied that according to the Lübeck Law, planting trees in front of houses was prohibited. Then Peter bestowed upon Hukk and his descendants the privilege of growing two trees in front of their home. This explains the two Linden trees that can be seen in front of the House of the Burgomaster Hukk on Lai Street in Tallinn.

Tallinn's Old Town is a UNESCO World Heritage site known for its well-preserved medieval structures and cobblestone streets. Exploring these historical areas with a local guide who can provide you with the most accurate and exciting information about the different buildings and their histories is always recommended.

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St. Olaf's Church (Oleviste kirik in Estonian) is a historic landmark in Tallinn, Estonia, and is among the top 20 tallest churches in the world. Today, it is the second tallest structure in Tallinn, surpassed only by the Tallinn TV Tower. To honour the church's historical stature, Tallinn's authorities have enacted regulations prohibiting the construction of skyscrapers in the city centre that exceed the height of St. Olaf's spire.

The church's origin dates back to the 12th century and is linked to a fascinating legend. It is said that many centuries ago, the people of Tallinn wanted to build a large church with a spire so tall that it could be seen by foreign merchants sailing by sea. An unknown master builder agreed to take on the project but requested ten barrels of gold as his fee. When the townspeople found the price too high, the builder offered an unusual condition - if they could discover his name, he would not charge them for his work. As the church construction neared completion, the townsfolk sent a spy to the builder's wife. The spy overheard a lullaby she sang to her child that revealed the builder's name, Olev. When the townspeople called out to the builder by his name as he was installing the cross at the top of the spire, he was so shocked that he let go of the cross, fell from the scaffolding, and turned to stone upon hitting the ground. From his mouth emerged a frog and a snake.

Historically, St. Olaf's Church is believed to have been established on its site in the 12th century, where a trading yard of Scandinavian merchants was located during the Middle Ages. However, the first written mention of the church dates back to 1267, when it was protected by St. Michael's Cistercian women's monastery. In the 1420s, the church underwent significant reconstruction, transforming the longitudinal baptistery into a basilica and constructing new vaults and choirs.

During the Reformation movement in 1524, aimed against the abuses of the Catholic Church, the Catholic clergy was expelled from the churches of Tallinn. On the night of September 14, 1524, a crowd of reformists plundered the interior of St. Olaf's Church. However, the exterior of the church remained intact.

The spire of St. Olaf's Church, which today stands at a height of about 123.7 meters, was at one point in the 16th century reportedly 159 meters tall, making it one of the tallest buildings in the world. The observation deck offers panoramic views of Tallinn, and to maintain this historical symbol, the city has prohibited the construction of any building taller than the church in the city centre.

The church hosts an active congregation and is used for regular worship services, and its acoustics make it a popular venue for concerts featuring Estonian and international musicians. Despite its turbulent history, the church remains an iconic part of Tallinn's skyline and a significant symbol of its rich history.

Photo By Olga Itenberg

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The "Three Sisters" are an outstanding example of Tallinn's architectural heritage, standing as an engaging fusion of medieval and contemporary design aesthetics. Nestled on Pikk Street, within the city's medieval Old Town—a UNESCO World Heritage Site—these three buildings are a testament to Tallinn's rich history and cultural vibrancy.

Initially constructed as individual merchant houses in the 14th century during the zenith of the Hanseatic League's influence, these structures have been meticulously preserved and adapted to the city's evolving requirements. Over the centuries, they've been home to esteemed individuals ranging from wealthy merchants and guild elders to city councillors, mayors, and notable figures such as the renowned builder Hinrik Swalberg.

Despite numerous renovations and the passage of time, the exterior facades of these buildings have impressively maintained their 15th-century appearance. This architectural preservation showcases the exceptional craftsmanship of the period and provides a vivid glimpse into Tallinn's historical past.

Internally, however, these structures have witnessed several modifications. Each transformation mirrors the changing aesthetic preferences and practical necessities of the times, reflecting the city's progression and its inhabitants' evolving needs.

A significant refurbishment in 2003 led to the merging these three houses into a unique boutique hotel, adding a layer of modern comfort to the centuries-old structures. This harmonious blend of historical charm with contemporary hospitality design underscores Tallinn's enduring respect for its past while enthusiastically embracing the present and future.

Today, the "Three Sisters" remain proud custodians of Tallinn's architectural legacy and rich cultural history. As they stand, they offer an engaging dialogue between the past and present, effortlessly merging historical grandeur with contemporary luxury, captivating locals and visitors worldwide.

Photo by Sailko. CC BY-SA 4.0

The Fat Margaret Tower, officially named "Paks Margareta" in Estonian, is a significant historical landmark and a proud representation of Tallinn's rich architectural heritage. Built as part of the city's defensive fortifications during the 16th century, this structure initially functioned as a protective gateway for the harbour.

The journey to construct the imposing defensive structure we see today began in the second quarter of the 14th century. A square tower with an arched gateway, the city's first gate, was erected on the road leading to the harbour when the district around St. Olaf's church was incorporated into the city. Unfortunately, this original structure did not survive to the present day.

Between 1434 and 1460, additional fortifications, including two slender round towers flanking the gate across the moat, were added. These were characteristic of Tallinn's architectural style at the time. The gate underwent significant reconstruction in the early 16th century. In 1510, the eastern round tower was replaced with the cannon tower known today as Fat Margaret.

Fat Margaret was a four-story construction with a battle platform. The ceilings within the tower rested on a central pillar, and in line with the principle of horizontal defence, cannons were also placed on the first floor. In addition, the gun chambers were equipped with ventilation channels. At the same time, a defensive base was added to the western tower of the fortifications, and later, a second wall (Zwinger) with two rows of embrasures was constructed in the northeastern corner of the city wall.

Two legends are associated with the tower's name, Fat Margaret. One story tells of a large woman named Margaret who cooked for the fortress guards. Unfortunately, she prepared unpalatable food and scrimped portions, leaving the soldiers hungry. In retaliation, the soldiers decided to wall her up alive within the tower. However, a more romantic version of the legend tells the tale of a peasant's son, Herman, and a fisherman's daughter, Margaret, who were in love. They would stroll hand-in-hand through the city in the evenings but were constantly obliged to part and leave the town before midnight due to a curse.

In its varied history, Fat Margaret has served as a storehouse, a barracks, and a prison. Now, it houses the Estonian Maritime Museum, an extensive repository of the nation's maritime history, ranging from ancient shipwrecks, navigational instruments, and marine artwork to nautical clothing. From the rooftop viewing platform, visitors are treated to panoramic views of Tallinn's Old Town and its harbour, seamlessly blending a historical journey with a visually captivating experience.

Fat Margaret is a significant part of Tallinn's architectural legacy today, perfectly merging the city's historic past with its vibrant present, captivating locals and visitors worldwide.

Photo By Jennifer Boyer from Maryland, USA - Paks Margareeta (Fat Margaret)Uploaded by Magnus Manske, CC BY 2.0

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