Tallinn: An Offbeat Travel Guide for History Lovers

The early history of Tallinn is somewhat murky in the absence of written sources. The Estonian History Museum questions its status as a kingdom, preferring to leave the possibilities open for discussion. While Estonia did have noble classes, it had no native royals; however, successive occupying powers gradually altered the face of Estonian society.

The Germanic name Reval was used for seven centuries after the Danish conquest of the city in 1219 – since the invasion of the Teutonic Order and during the height of the Hanseatic League's power, until 1918. The region was historically called Livonia, home to the Livonians, comprising parts of present-day Latvia and Estonia.

The Polman family, with its noble Baltic German heritage, found its way from Germany to Estonia, where one branch of the family eventually matriculated into the Estonian nobility (No. 112.) Significantly, Jürgen Polman was born here and built a life and career that eventually connected the family to Sweden. He was among the soldiers fighting for Sweden, and was imprisoned during the Polish-Swedish War, possibly in Tallinn. Another notable character is Reinhold Wilhelm von Pohlmann, a celebrated jägermeister held in high regard by Russian empress Catherine the Great.

This guide is arranged roughly in order of historical events rather than distances or proximity. To plan the best routes, use our Google map. 

The first Estonian uprising – Padise

It might seem a little too offbeat, maybe even strange, to begin a Tallinn travel guide outside of the city. But bear with us. As the site of the first and most significant uprising of Estonians against any invading power, the monastery at Padise holds historical and contextual value. Located in Harju county, an hour's direct bus ride from Tallinn, Padise is home to a 13th century monastery, permitted by Erik Menved, King of Denmark, in 1305. In 1343, the monastery was attacked by peasants who were against Danish rule[[1]], and later rebuilt as a fortified complex. It was occupied by the Teutonic Order, and Russian and Swedish troops during the Livonian War in the 16th century. 

The monastery was owned by Sweden until 1622, and then donated to the Archbishop of Riga, Thomas Ramm, for his services in battle. The monastery became a residence, and when it burned down from a lightning strike in 1766, a manor was built in the vicinity. It was renovated in the 19th century and now hosts events, accommodation and a spa. Renovations also began at the monastery in 2020, and it is open for visits. 

It is to Padise that the Polmans, a Baltic German family, trace their first home in Estonia. Hans Polman was a county clerk here in the 16th century, and his son Jürgen would go on to become the steward and commander of Padise in 1613; his descendants later migrated to Sweden. 

The seat of power – Toompea Castle

Toompea Hill was the centre of Tallinn, which grew gradually around it. A castle existed here since at least the 13th century, initially only for refuge rather than settlement. With the Danish conquest in 1213, a stone castle was established. Since then, though it changed hands several times[[2]], the castle has been the location from which Tallinn was ruled or governed. It now serves as the parliament of Estonia. 

Having hosted several rulers, it has been modified over the years, and comprises several distinctive elements, including the Tall Hermann tower which is adorned by the national flag. The amalgamation of different styles incorporated by various rulers provide a chronicle of the history of Estonia, from medieval and gothic to baroque, making it the “only Expressionist style parliamentary building in the world.” The Castle is open to visitors and offers free guided tours.

Entering medieval Tallinn – Viru Gate

The entrance to the Old Town is flanked by two red-capped, vine-encased stone turrets – the barbican is the remnant of a 14th-century defence fortification surrounding the city centre. The gate itself was demolished, as were the walls[[3]] around it, to accommodate a rapidly developing and modernising city[[4]], but the towers were retained.

Located at the threshold that separates the modern and medieval parts of Tallinn, Viru Street is lined with florists, souvenir shops and cafes. Musumägi, colloquially known as Kissing Hill, spreads to the left. It is now a small park built on the remains of a bastion[[5]] that was never completed, abandoned in 1686. It features sculptures by Estonian artist Tauno Kangro, and offers a moment of respite before stepping into the irresistible magic of the Old Town.

The celebrated heritage of Vanalinn – Town Hall Square

The Old Town is a UNESCO World Heritage Site for a reason – walking its cobblestoned streets feels like traversing a fairytale. Despite being bombed during World War II, much of the town is preserved and dates back to the 13th century, with medieval and Hanseatic planning and architecture. It comprises two distinct regions – Toompea Hill, historically home to the gentry, and an autonomous Lower Town; they are separated by a gateway. 

In the main square, the Town Hall (Raekoda) built in 1404[[6]] is unmissable, topped by its unique weather vane. The oldest surviving town hall in northern Europe, it is now a venue for exhibitions and concerts. Opposite it is Europe's oldest pharmacy and Estonia's oldest working commercial and medical establishment, Revali Raeapteek. The claret wine created here in 1467 is still sold, as is marzipan, as well as regular items sold at pharmacies. It also houses a museum.

A historically long street – Pikk 

Pikk Street is the oldest street in the city, dating back to at least the 14th century. The name translates to “long street” (German: Langstrasse) – it is nearly a mile long (723m), and was a main street during medieval times, connecting Toompea and the lower town till the sea. 

Many colourful and awe-inspiring medieval buildings line both sides of the cobblestone. Various architectural eras are represented, including Gothic, Renaissance and Baroque. Quite a few buildings are marked as “National Monuments”, including number 44, a residential building dating back to at least 1401[[7]].

The three-storey house with its pastel green exterior and white shutters once belonged to Reinhold Wilhelm von Pohlmann. It was reconstructed in the 17th to 19th centuries, with refurbishments including design upgrades to the windows and roof. Von Pohlmann bought the house in 1777. A decade later, preparations were made to host Princess Auguste of Brunswick – who was under his care at an estate in Lohde after fleeing an abusive husband with the assistance of Catherine the Great – at Pikk St during the winter months.

The Great Guild – Estonian History Museum

A historic Gothic building completed in 1410, the Great Guild Hall at 17 Pikk St. has played several roles in Tallinn's story. It was built for a brotherhood of married merchants[[8]] called the Great Guild, and was a significant site when Tallinn joined the Hanseatic League at the end of the 13th century. In the 19th century, it became a stock exchange and a venue for commerce and the arts. Significant events held in this building include the screening of the first film in Tallinn in 1896.

It is now home to the Estonian History Museum. Each room tells a story without a beginning or end, and the museum can be navigated in any order. The curators favour an exploratory approach – asking questions rather than providing answers, they invite the audience to ponder and engage. The former excise chamber of the building exhibits numismatics, while the former treasury houses temporary showcases of rare objects. A “chamber of legends” tells stories connected to material history and heirlooms, while the basement explores the history of the Great Guild and the building. Behind the museum, a short pathway contains a timeline of important events in Estonian history in the form of stone plaques. 

Enter Lutheranism – St. Mary's and St. Olaf's 

St. Mary's Cathedral, the oldest church in mainland Estonia, was built in the 13th century. It was the sole building to remain standing in a devastating fire in 1684, but had to be extensively rebuilt. It was initially a Roman Catholic cathedral, but switched to Lutheranism during the Protestant Reformation in the 16th century.[[9]] It holds several tombstones and sarcophagi, as well as some significant burials.

St. Olaf's Church stands out as the tallest medieval building in Tallinn's skyline, with a spire at 123 metres. It dates back to the 13th century, and its role changed several times in history – like St. Mary's, it shifted from Roman Catholicism to Lutheranism, and was later used by the KGB in the 20th century for radio and surveillance operations. Since the 1950s it has been used by local baptists. The spire of the church once stood even taller[[10]], and was struck by lightning several times, resulting in at least three fires that burned down the church. The observation deck offers stunning views of the city. 

Russia takes over – Kadriorg Palace

Russia successfully defeated Sweden and gained control of Tallinn in the Great Northern War, following which Peter the Great began to plan a palace in the city. The construction of Kadriorg Palace – meaning Catherine's palace – began in 1718 and was completed in 1725, the year of Peter's death. However, interest in the palace waned even upon its completion, and over the years, many interior renovations have taken place. The architecture of the vibrant building is in the Petrine Baroque style favoured by Peter and found widely in St. Petersburg. It was designed by Italian architect Nicola Michetti, and features stucco interiors that still survive. The palace is now home to the Kadriorg Art Museum, exhibiting collections of European and Russian art from the 16th to 20th centuries.

Baltic-German representation – Estonian Knighthood House

The Estonian Knighthood was a collective of Baltic German nobles who had effectively ruled Estonia since the 13th century, when they occupied the country. The Knighthood House, where they gathered for celebrations, was destroyed twice in fires, and a third iteration proved too small. The current building, recently renovated, was built between 1845 and 1848. It served several purposes: as the Estonian Ministry of Foreign Affairs after 1920 (noble privileges were stripped when the country became independent), and as the National Library between 1948-92. In 1993, it temporarily housed a part of the Kadriorg collection while the palace was renovated; it then became home to the Estonian Academy of Arts for a few years. It is now the Estonian Statehood House, meant for receiving foreign dignitaries and hosting state events.

The Polman family was originally Baltic German. It is believed that one of Jürgen Polman's sons, Claus, was the progenitor of the von Pohlmann family line, registered by Reinhold Wilhelm von Pohlmann in 1754 at the Knights’ House under No. 112.[[11]]

Marzipan at the oldest cafe – Maiasmokk  

Maiasmokk Cafe at 16 Pikk St. has the distinction of being “the oldest continuously operating café in Tallinn and probably in all of Estonia”. It dates back to 1864, when it was owned by a Baltic German confectioner, George Stude, known for his unparalleled marzipan. But the building is even older, and was previously a bakery and confectionary as early as 1806 owned by Swiss Lorenz Cavietzel. 

Marzipan, a confection of almonds and sugar, has a long history in Estonia. Originally considered a medicine, it was manufactured at the pharmacy in the Town Hall Square. Later, during the Hanseatic period, it began to be made at confectionaries, including by Cavietzel and Stude, the latter of whom was renowned for his exclusive marzipan products across Livonia and in Russian courts. Cafe Maiasmokk still makes this confection “exactly as it was hundreds of years ago", and even conducts workshops. A renovation in 1913 gave the cafe its current aesthetic, well worth a visit for its unique history and sweet creations.

The Russification of Estonia – Alexander Nevsky Cathedral 

Completed at the turn of the 20th century, the splendour of this Eastern Orthodox cathedral marks the pinnacle of Russian power in the country, and has consequently faced several calls for demolition. Russification was a term referencing “the policy of enforcing Russian culture on the vast numbers of ethnic minorities that lived in the Russian Empire,”[[12]] and this cathedral was a symbol of exactly this, from its opulence to its location dominating the hill. Nonetheless, the cathedral – which was built in the Russian Revival style with five domes and an ornate interior, with eleven heavy church bells – was restored after Estonia became independent. It is the largest cupola church in Tallinn.

The importance of records – National Archives of Estonia

Not a historical site in itself, the National Archives (Rahvusarhiiv) were founded in 1999 and include branches in Tallinn and Tartu, as well as reading rooms and film archives. Their origin was the Historical Archives, founded in Tartu in 1920. During Soviet rule, local archives continued their work but were governed by Russia until independent management was restored following the Archives Act of 1998. The National Archives house historical and archival information for research, as well as genealogical information. Many of their collections are digitised and are available online. The National Archives are relocating in 2025.

Also of note are the Tallinn City Archives (Tallinna Linnaarhiiv), which originated in 1883 from the collections of the Town Hall. Its history includes serving as the city museum, a research institution, and meeting venue of the Tallinn Historical Society. A significant document pertaining to the parenthood of the Polman patriarch, Jürgen Polman, can be found amongst its records.

[[1]]: Major damage was caused to the monastery; monks were killed as well as Estonians in the retaliation. However, it caused Denmark to sell much of its northern Estonian lands.

[[2]]: The King of Denmark sold Estonian lands including Tallinn to the German Order (Teutonic Knights) in 1346.

[[3]]: The first wall was built in the 13th century.

[[4]]: The population of Tallinn was less than 1,000 in the 14th century, but grew six- or sevenfold in the late middle ages.

[[5]]: Bremeni Bastion, converted into a park in 1897.

[[6]]: Current building; its history dates back to the 12th century

[[7]]: Monument register number 3046 https://register.muinas.ee/public.php?menuID=monument&action=view&id=3046 

[[8]]: Merchants who were bachelors could join the Brotherhood of the Blackheads. The House of the Blackheads is located at 26 Pikk St.

[[9]]: Lutheran preachers arrived in the 1520s and several churches were ransacked; eventually the religious order was reassembled.

[[10]]: https://visitestonia.com/en/st-olaf-s-church-tower-and-observation-platform

[[11]]: He successfully presented evidence of the family’s noble origin to the Matrikul Commission of Estonia. Along with his brothers Otto, a cornet, and Gustav, a lieutenant colonel in Russian service, Wilhelm was included in the Estonian nobility.

[[12]]: “The Russification of National Minorities”, BBC Bitesize, https://www.bbc.co.uk/bitesize/guides/z6rjy9q/revision/7#:~:text=Russification%20was%20the%20policy%20of,Poles%2C%20Lithuanians%20and%20the%20Ukranians, accessed on 6 March 2025