The Magic & Trapping of Tallinn

Given my self-professed love for Estonia, I surprise myself by not writing a post on Tallinn until now. Like many travelers before me, Tallinn was my first introduction to Estonia and the Baltic states when I first visited in 2012. At the time, I was on a traveling fellowship with my graduate school; the thesis of my project was to observe and document the development of post-Soviet architecture. So it was ironic that central Tallinn has none of the post-soviet architecture I came to study. Often described as storybook-like, this city is one of the ”best-preserved” medieval cities in Northern Europe and among the most photogenic capital cities in the world. I suspect 90% of foreign tourists to Estonia did not bother to venture beyond the border of Tallinn’s charming old town.

The view Tallinn’s skyline from the Helsinki-Tallinn ferry.

Central Tallinn is a cultural and architectural delight inscribed as a UNESCO World Heritage Site. Today’s central Tallinn has been inhabited for more than five thousand years, but it was not until the 13th century that the town began to develop after the knights of the ruling Teutonic Order constructed a castle on top of the hill. Over the subsequent centuries, Tallinn became a major trading port of the Hanseatic League, the most important free trade zone of the Middle Ages. The network of like-minded semi-autonomous cities is often regarded as Europe’s first “transnational” trade alliance.

Being the northernmost city within the Hanseatic League, Tallinn holds an enviable position in funneling trades from the Russian interior to the Atlantic. Over the decades, it became one of the wealthiest cities in the Baltic, far surpassing the provincial Helsinki at the time. Lucky for us visitors, the city preserved its architectural heritage and riches despite Estonia’s troubled history. While one could perfectly enjoy the charm of Tallinn without learning much about the history of Estonia, I believe a brief survey of Estonian history would give much deeper meaning to this magical place.

The Lower Town

The Old Town that we know and love today comprises two distinct sections: the Lower Town and the Upper Town. The two used to be two separate administrative units. The upper town, known as Toompea, is reserved for the political class of the dominion. It remains the seat of the Estonian Government today. The lower town was home to Tallinn’s business class, principally the Baltic German traders that controlled the trades throughout the Hanseatic League. The two towns may seem conjoined, but walls and gates still separate them.

Viru Street is the main pedestrian drag of Old Town Tallinn.

Known as Ravel for much of its history, Tallinn may be a symbol of a prosperous Estonia today. But that was not the case for much of its history. Throughout its history, the land of the Estonian people was passed among the great powers of Northern Europe. All in all, the area of modern Estonia was ruled by the Danes, the Swedes, Teutonic Knights, German Livonia, Polish-Lithuanian Livonia, the Russian Empire, Nazi Germany, and finally the Soviet Union. For much of history, ethnic Estonians have been considered serfs in the feudal system, with Baltic Germans being the landowners. Serfdom was not abolished until 1816 under the Russian Empire.

Lower Town of Tallinn is bustled with great energy days or nights.

As serfs, ethnic Estonians welded no political or social status on their own land. Tallinn's grand merchant houses and town hall were constructed with Estonian labor for the Baltic Germans. Tallinn carries the same characteristics as Germanic cities like Lübeck or Gdansk. While the Estonians provided all the labor for the town’s construction, few had the privilege to live with the city’s wall. Walking through the streets of the Lower Town, we could see numerous “guild halls” dedicated to various trades. The Great Guild is the most significant, Gothic monument to the Hanseatic League. The grand building was the home of the 19th-century Tallinn Stock Exchange and now is home to the Estonian History Museum.

While the city suffered aerial bombardment during World War II, just less than ten percent of structures within the medieval walls were constructed after the war. The people of Tallinn celebrate and capitalize on the city’s medieval heritage well. After Estonia’s re-independence after the collapse of the Soviet Union, Tallinn underwent a remarkable revitalization. The city’s historical houses were restored; the cheerful colors of Tallinn reemerged after decades of stoic slumber during the Soviet years.

The Soviet Union had a somewhat uneasy relationship with historical heritage. Its state atheism and the anti-bourgeois founding often meant that its historical cities were often neglected either by design or not a priority for the government. This attitude seemed to be particularly pronounced in the three Baltic republics. Most Estonians are grateful that Tallinn survived the Soviet period and escaped the ruthless urban renewal of the 1960s and 1970s. Nowadays, the people of Tallinn take full advantage of its medieval heritage. It has become a magnet for tourism. In the most touristy part of town, medieval-theme restaurants with costumed wait staff seemed popular with visitors. However, they do appear more “pan-medieval” than Estonian.

No matter where you entered the Old Town, it is only inevitable that you would end up at the Town Hall Square. It was Tallinn’s main piazza and was surrounded by grand medieval buildings. This is also where all the tour groups from cruises seem to converge. The scheme was more crass tourism than authentic ambiance. All around the square are outdoor cafes and restaurants eager for your patronage. While it could be a bit of a turn-off for some, I could appreciate this convivial scheme as a triumph of capitalism. After all, the popularity of Tallinn is key in securing vital finance for the Old Town’s upkeeping.

Looking beyond the tourism economy, the square holds many historical claims that still resonate today. The Old Town Hall Pharmacy is at the northeastern corner of the square (Raeapteek). This historical pharmacy is recorded as the oldest continuously operating pharmacy in the world that is still at its original location. Coincidently, it also happens to be the oldest business in Estonia. Attached to the pharmacy is a small medical museum that may interest some visitors. However, you could still go in to get yourself Tylenol here.

What makes Town Hall Square “potentially” special is that this is allegedly where the world’s first Christmas tree was erected. The Christmas tree was a tradition initiated by the Brotherhood of the Blackheads in 1441. The brotherhood is a guild of unmarried male merchants, ship owners, and foreigners active in Latvia, encompassing much of modern Estonia and northern Latvia. The brothers would dance around the giant spruce tree to celebrate the holiday. There is a dispute between Tallinn and Riga as to which city had the first Christmas tree. If you had the good fortune to visit Tallinn during the holiday season, Tallinn has one of Europe's most romantic Christmas markets.

As the name suggests, the square is named after Tallinn’s historic town hall. Constructed in the 15th century, the Old Town Hall is the most renowned landmark in the lower town. While no longer functioning as the seat of the municipal government, it is the most beloved building in the Lower Town. The building has numerous interesting architectural details, such as bright green dragon gargoyles and a weather vane with three eggs. But the most important of all its decorations is the Old Thomas (Vana Toomas), a decorative weather vane placed on the pinnacle of the spire.

The tale of Old Thomas is well-known in Estonia. Thomas was an Estonian peasant boy who, by chance, came across a crossbow competition among the Baltic German merchant class. After no German could hit the wooden parrot on top of a high post, Thomas volunteered and got hit the parrot on his first try. Because of his ethnicity, Thomas was not eligible for the top prize in the contest. But impressed by Thomas’s marksmanship, the mayor appointed him the city’s guard, an honor typically bestowed on Baltic Germans. Thomas continued on with a distinguished military career and became a popular figure among Estonians. Years later, some locals noticed that the future on top of the town hall weathervane looked remarkably like Thomas. So, the name sticks to this day. The Old Thomas is now considered to be the guardian spirit of Tallinn and one of the most beloved figures in Estonia.

As magnificent as the Town Hall Square may be, I don’t think it could hold a candle to Tallinn’s medieval fortification. Constructed by the order of the Queen of Denmark, Margaret Sambiria, the walls were enlarged or strengthened in subsequent centuries. With over two dozen medieval towers still intact, it is considered one of Northern Europe's best surviving medieval defense systems. Brian and I have seen plenty of medieval fortifications, but none is as romantic as those in Tallinn. The red conical roof looks straight from a classic Disney fairytale.

To appreciate the majesty of the fortification, head to the best-preserved section along the northwestern edge of the Lower Town. The outer perimeter is lined with a public park called Towers' Square (Tornide Väljak). This wall section ran approximately 1.2 miles and seemed perfect for photography. The beautifully landscaped park provides a much-needed refuge from the bustle of modern tourism. A series of exhibits of contemporary artworks are dotted next to the walkway. It was the most beautiful spot in Tallinn.

For any fan of medieval warfare, I recommend visiting the Hellemann Tower, which is open to visitors. Visitors could climb the round towers and walk along a covered walkway atop the wall for a few euros. The viewpoint from the top of the wall was magnificent. While visitors today could admire Tallinn's beautiful tile roof and church spires, it is also a somber reminder that this is where some of the tough sieges were fought centuries ago.

Speaking of churches, one church in Tallinn towers over the whole city: Saint Olaf’s Church. Dedicated to King Olaf II of Norway, who was later canonized as Saint Olav. The church's construction began in the 13th century to serve the Scandivanian community of Tallinn. Over the centuries, the church was repeatedly struck by lightning and then rebuilt. By many accounts, the impressive tall spire made it the tallest man-made structure in the world. From the moment we arrived by ferry, the dramatic spire dominated the skyline and made it distinctly Tallinn.

The soaring vestibule of Saint Olaf’s Church.

Like most religious structures in the region, Saint Olaf’s Church was whitewashed during the Reformation. The absence of decorations and iconography makes the church look especially barren for foreboding. Now used by Tallinn’s Baptist congregation, the church was extensively refurbished as part of the government-sponsored Tallinn Church Renaissance Program. With Estonia being the least religious nation on the planet, the city saw it necessary to safeguard its historic churches' architectural and cultural heritage. Otherwise, these magnificent churches would succumb to the attrition of time.

The top of Saint Olaf’s Church offers a wonderful overview of Tallinn’s medieval fortification.

Although I enjoyed the whitewashed interior, the highlight of the visit was hiking up the church’s bell tower. At 60 meters, the observation platform could feel scary in places, even when a steel enclosure is fully enclosed. To see the actual spire up close was quite amazing. It was quite amazing to see how medieval builders managed to construct such a supertall structure. For reference, the tiny golden orb at the top of the spire measures four and a half feet in diameter. We could also see the entire fortification system from the platform. It was easily the most worthwhile bell tower climb I did.

With so many historic buildings around, Tallinn’s Lower Town packs so many surprises. The hidden courtyards nestled among the narrow lanes are some of the loveliest corners. The most famous among them is Saint Catherin’s Passage. This short, narrow lane is often regarded as the most romantic street in Tallinn. The street is named after the Guild of Saint Catherine, which has been revived in modern times at this same spot. Local artisans set up their studios here to allow visitors a peek into their crafts.

Toompea Hill

Perched high above the Lower Town is a limestone bluff known as Toompea. The hill occupies the most strategic location in Estonia and has long been the perch of the rulers of Estonian land. Inhabited first in the late Iron Age, Toompea was officially fortified by the Livonian crusaders in the 12th century. At the time, various wealthy owners of manors opted to reside inside the castle instead of in the countryside because of the fear of the uprisings of Estonian serfs. Toompea Castle became the most fortified fortress in Livonia and was subsequently converted into an administrative palace during Swedish rule.

Historically, Toompea was only accessible through two passages: Long Boot (Pikk Jalg) and Short Boot (Lühike Jalg). Ascending the passway through the medieval gates creates a sense of reverence. Toompea’s historical significance could not be understated. According to common Estonian mythology, Toompea is a funeral mount for Kalev, Estonia’s founding hero, constructed by his wife, Linda. Since Kalev and Linda are considered the mythical ancestors of the Estonian people, Toompea’s place in the Estonian psychic is deeply rooted.

Interestingly, Toompea played a historic role in the history of Denmark. Legend had it that Demark’s red and white national flag originated here. A red flag with a white cross descended from the sky during the Danish’s battle with the Estonia tribes in 1219. The flag appeared just as the Danish forces were on the retreat. The flag provided a much-needed morale boost, ultimately leading to a Danish victory over the Estonians. This flag ends up being the oldest national flag in existence today.

Tall Hermann is an enduring symbol of Estonian sovereignty and freedom.

Much of the original Toompea Castle was demolished in the 19th century when Tallinn was incorporated into the Russian empire. The part that survived was a lone defensive tower called Tall Hermann (Pikk Hermann). The tower is widely regarded as a symbol of Estonian sovereignty. The flagpole atop this tower is considered the most important in the country. The lowering of the Soviet flag in 1989 here signified the beginning of the end for the Soviet empire. Raising and lowering the national flag at Tall Hermann are still carried out daily with great reverence. Every morning at sunrise, the Estonian flag was raised to the music of the national anthem. At sunset, it was lowered with the music of Mu Isamaa On Minu Arm, the underground anthem of Estonia during the Soviet time. On February 24th, Estonians gather at the base of Tall Hermann to participate in the Independence Day flag-raising ceremony at dawn.

With Tall Hermann being the few remnants of the medieval caslte, much of the Toompea was converted into administrative palaces. The most important among them would be the parliament building of Estonia. The pink-colored building has been the seat of the parliament since Estonia’s founding in 1918 and was the meeting place of the Supreme Soviet of the Estonian SSR from 1940 to 1992. One of the biggest regrets of my visits to Tallinn was skipping the free guided tour of the Toompea Castle and the Estonian Parliament (Riigikogu). Besides my personal interests in Estonian history and politics, the inner section of the parliamentary complex is distinctive in architectural style. Designed by Estonian architects Eugen Habermann and Herbert Johanson in 1922, this is the world’s only parliament building in Expressionist style. This is not only the first building in Estonia to be designed with electrical wiring but also designed with artificial lighting in mind.

The neoclassical facade of the Estonian Parliament (*Riigikogu*).

The parliament building is also the site of a pivotal moment in the Singing Revolution. On May 15, 1990, five thousand anti-independence activists (mostly ethnic Russians) stormed the Estonian parliament in an attempt to overthrow the independent-minded Supreme Soviet. The prime minister got on the radio and called for citizens to help repel the attackers. Upon the arrival of Estonian residents, Russian protestors were sequestered inside the courtyard of the parliament building. A bloody conflict seemed unavoidable. Remarkably, the Estonian citizens allowed outnumbered Russians to leave the area without violence or reprisal. Estonians often recounted this incident to symbolize the principle of political non-violence.

Speaking of Estonia’s ethnic Russian minority, the percentage of ethnic Russians living in Estonia steadily increased after Sweden ceded the territory to the Russian Empire. Systematic Russification was carried out to streamline the administration of the empire. Until this point, the daily running of Tallinn and the Estonian territory has been run by Baltic Germans, regardless of which empire the city belongs to. Russian Empire put an end to that. Saint Petersburg was eager to flex its cultural muscle over its dominion. The best demonstration of this effort was constructing a massive orthodox church across from the governor’s palace, the current parliament building.

Based on its architectural merit, Alexander Nevsky Cathedral is a beautiful building. The Russian Revival style church has all the hallmarks of the beauty we associate with an orthodox church. However, it should be evident to everybody that this church is really out of place among all the Lutheran churches of Tallinn. For many Estonians, the church is an instrument of political intimidation. A massive Russian church opposite Estonia’s national parliament did not endear Russians with the ethnic Estonians. Before the Soviet invasion, the Estonian government planned to demolish the cathedral. However, it was never carried out due to the lack of funds and protests from the orthodox community. An Estonian politician once complained that tourists often neglected the presence of the parliament building because they were distracted by the Orthodox cathedral.

Besides the national parliament building, Toompea Hill is home to numerous government ministries and embassies. For most visitors, it is refreshing to see how humble many government buildings are. Considering Toompea’s political importance, the entire neighborhood has a surprisingly residential feel; many embassies are housed in small medieval houses with little apparent fear of security. Needless to say, the American embassy was not among them.

As an American, I sometimes forget how distant national politics seem to us. For a nation of 1.4 million, Estonia has a pretty different relationship between its citizens and politicians. Given my fascination with Estonian politics, I may be one of the few American tourists who could recognize Estonia’s president and prime minister on the street. And sure enough, I saw a guy in an Estonian tricolored shirt jogging toward us. I quickly recognized that it was Taavi Rõivas, the prime minister of Estonia from 2014-16. I remembered seeing footage of him welcoming President Obama for a state visit not far from here. I don’t think I have ever been in such physical proximity to a national leader like this before.

Spire of the Church of the Holy Spirit and the National Song Festival Ground in the background.

For most tourists, the main draw of Toompea would probably be the Patkuli Viewpoint. From this perch, we have a panoramic view of the Lower Town. The vista is unparalleled, from the fortification walls and Saint Olaf Church to the Tallinn TV Tower in the distance. It looks like a view taken from the Pixar or Dinsey fairytale. Comedian John Oliver once compared Tallinn to a place where “from the looks of it, they still worry about Shriek attack.” While I think Oliver’s satire about Estonia’s technological progress is ironic, I certainly don’t blame people for considering Tallinn to be an anachronistic place. I suspect few tourists realize that Estonia is among the most technologically savvy places in the world!

Steps from Patkuli Viewpoint is another observation platform: Kohtuotsa Viewpoint. You have an excellent view of the Gulf of Finland and Tallinn’s busy port from that spot. But the highlight for me was a close-up view of the terrace of Steinbrook House. Although this neo-classic palace looks just like any other, an Estophiles like myself knows this is the working office of the Estonian prime minister. That was the terrace where Estonian leaders would bring foreign dignitaries during visits to Tallinn. It is the Estonian equivalence of the White House balcony, a fact that is lost on most visitors.

The Modern Face of Old Town

Because Tallinn is one of the best preserved medieval cities, people are often surprised to see a collection of fine modern buildings sprinkled across the old town. As much as we like to think a city could be frozen in a specific historical period, Tallinn remained a living city that still evolves with modern life. Yes, you can get American chains like McDonald’s and Starbucks in Old Town. But that doesn’t mean they necessarily stick out like a sore thumb in the historic city. The architecture and signage are carefully integrated into the urban fabric in good European fashion. While many visitors may be disappointed with the modern architecture, I love how well Tallinn handled it.

In addition to contemporary architecture, there are probably half a dozen Soviet-era buildings of importance. Among them, Sõprus Theater is particularly the most handsome example of Soviet Estonian architecture. In my study of Soviet architecture, I am particularly fascinated by how Soviet architecture fits into the cultural psyche of contemporary Estonia. With the ongoing war in Ukraine front and center nowadays, the governments of the Baltic states were keen to remove the symbol of their own history of Soviet occupation. While I wholeheartedly agree with the government’s decision to remove Soviet memorials, I am quite worried that Soviet-era architecture will meet a similar fate eventually.

Freedom Square and the War of Independence Victory Tower.

At the edge of the Old Town is arguably Estonia's most important civic space: Freedom Square. During the Russian imperial period, a massive statue of Peter the Great was erected here to commemorate Russia's capture of Tallinn. Since then, this has been where all the major national commemorations typically take place, from the May Day parade of the Soviet time to the recent massive protest against the 2022 Russian invasion of Ukraine. Although it has none of the charms of the medieval city, it is arguably more culturally significant than the more famous Town Hall Square. After all, Old Town Square was built for the Germans and was not really part of Estonian cultural tradition.

In so many ways, this is the paradox of Old Town Tallinn. What drew tourists in was not necessarily the essence of Estonian culture. Instead, Tallinn is a German Hanseatic town. Think about it: Estonians only began running Tallinn after the establishment of the republic in 1918. Tallinn’s Estonian identity is always a complicated topic. Tallinn is not considered the most Estonian city in the world; that title belonged to Tartu, Estonia’s second-largest city. Even to this day, ethnic Estonians are barely the majority in Tallinn. A small part of me was frustrated that most visitors missed the essence of Estonian culture on their day trip to Tallinn.

Timing your visit to Tallinn with the quinquennial Estonian National Song and Dance Festival is highly recommended.

So, what is the essence of Estonian culture? I watched separate interviews with President Kersti Kaljulaid and the Estonian Ambassador to the United States, Jonatan Vseviov. When asked about this question, their answer. Were music and language, respectively. As a lover (and an aficionado) of Estonian music, I wholeheartedly agree with their statement. For a small country, Estonia has a thriving domestic market for indigenous music. People take music seriously here. I was surprised to come across a professional Estonian-language production of the musical Spring Awakening. It may not sound impressive until you realize that more people live within the municipal boundary of Dallas than the number of Estonian speakers worldwide.

For anyone who cared to look beyond the obvious quaintness of Tallinn’s medieval facade, Tallinn’s music scene is thriving, and it was not too difficult to come across Estonian folk music. While writing this post, I reviewed my photos from my first trip to Tallinn nearly ten years ago. I just realized I took a serendipity photo of Sandra Vabarna and Tõnu Tubli all those years ago. They are members of the Estonian ensemble Trad.Attack!, which I have been following for the past few years. I first came across them because their music was the soundtrack of a dance routine at the 2019 Estonian National Dance Festival. It was a wonderful “AHA moment” for me.

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The Lower Town

Toompea Hill

The Modern Face of Old Town

Pirita - An Enchanted Slice of Tallinn

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