A historical walking tour of Tallinn's Old Town

Tallinn is a quaint, medieval city of less than half a million people, located on the cold shores of the Baltic Sea. To historians, it’s known as the best preserved medieval city in Northern Europe (more on that later!), to techies, it’s known as the birthplace of Skype, to Olympic fact collectors, it’s known as the only city to host the Olympics that was not located in a country that won the bid for the Olympics, and to Finns, it’s known as the place to get cheap alcohol. 

My first time I visited Tallinn, three years ago, I went on the behest of those in the latter category. I was in Finland, visiting my cousin, and people kept telling me to take the ferry to Tallinn. “It’s pretty…and the alcohol is cheaper!”. Expect to hear this a lot if ever visiting Helsinki. People from Finland actually go to Tallinn so much, we sometimes joke and call it southern Helsinki.

This is how it works up here in Northern Europe:

 Photo taken from @veryfinnishproblems

Photo taken from @veryfinnishproblems

Although I initially went for the cheap beer and to cross another country off my list, I fell in love with Tallinn’s Nordic-chill atmosphere combined with its post-Soviet vibes. I visit Tallinn so much (I swear it's not because I'm an alcoholic, I just love the city) my friends in Finland always joke that I need to actually do something with my obsession, like move there and become a tour guide. Until my big break through moment in the Tallinn tourism industry, I’ve decided to put together a walking tour of Tallinn’s Old Town: this tour averages 1.5-2 hours, but can be done much quicker or much slower, depending on what stops you decide to go into! It highlights all of the historical locations of Old Town, with a bit of folklore thrown in that I've learned from tours and talking to locals over the years. 

If you’re a tourist heading to Tallinn, there’s a 140% chance you’re arriving by boat. Luckily, the ferry terminal is extremely close to the Old Town, within walking distance. If you want to save your walking strength, there are taxis waiting outside of the terminal, but they have a reputation for severely overcharging. 

Historical walking tour of Tallinn route:

From the ferry terminal, follow all the Finns and Estonians towards the main road, then turn right and head towards Fat Margaret’s Tower (it’s about a 10-15 minute walk, depending which boat you come in on). Just before you arrive at Fat Margaret’s Tower, you will see a fairly odd looking sculpture on your left. It’s the Broken Line Monument, which was commissioned in honor of the sinking of the MS Estonia in 1994. The vessel, which had been in operation for 15 years without problem, sank on a route between Stockholm and Tallinn, killing 852 people. There are a lot of conspiracy theories surrounding the sinking: the Swedish government never allowed the boat to be recovered and exhumed, making many Estonians believe that they purposely took the ship down; other rumors started circulating that the boat was utilized to ferry naval armaments. 

 Broken Line Monument in Tallinn. 

Broken Line Monument in Tallinn. 

After the monument, you will see Fat Margaret’s Tower on your left. Head through her gates, making sure to look up at the relief dating from the 16th century, when Sweden took Estonia from Germany. (Estonian history involves a lot of other countries coming in on its land). Back in those days, the sea was a lot closer to the gate, so the gate was built not only for defense, but to impress visitors arriving to the medieval city. In the summer months you can buy a ticket to walk to the top of the tower (from the Maritime Museum down bottom) and get 360-degree views of Old Town and the harbor. Once you walk beneath the tower, look for The Three Sisters on your right, which showcases German Hanseatic influence from the 15th century. The first record of these merchant houses dates all the way back to 1362 and there have been recordings of guild elders and town councilors owning it ever since. 

 Fat Margaret's Tower

Fat Margaret's Tower

Continue past the merchant’s house to St. Olav’s Church, located on your right. In the summer months, it’s worth to head inside, pay the small price, and walk up the 200+ stairs to have a view of the city. It’s tiny, it’s exhausting, it’s steep, and it’s a little sketchy, but definitely worth it. The church is thought to have been built back in the 12th century and was, at some point, the tallest tower in all of northern Europe. During Soviet times, this tower was used by the KGB to block radio signals from Finland. Since Helsinki is not too far away, sometimes Estonians were able to pick up radio waves — I’ve heard stories from people telling me that they grew up not knowing what a pineapple was, but was always curious to see one because they heard about it on the radio; a large amount of older Estonians speak Finnish, or at least understand it, because of the decades under Soviet rule, being forced to learn Finnish to get any outside information. For all my Disney lovers, yes Olaf from Frozen has the same namesake! St. Olav’s Church was named after King Olaf II of Norway, also known as Saint Olaf. 

 The view from the top of St. Olav's

The view from the top of St. Olav's

 St. Olav's in the wintertime

St. Olav's in the wintertime

After exploring St. Olav’s, head back to Pikk Street (if you ever left). Pikk Street was first paved in the 15th century and used to be home of spice and meat sellers. A little further up at Pikk 59 you will find yourself at the former home of KGB local headquarters. This is where interrogation methods were put to use; you can still see some of the boarded up windows at the bottom of the buildings. It is now home to the the newly opened KBG Prison Cells Museum (official address for the headquarters and the museum is Pagari 1, but there is an entrance from Pikk). During it’s time, it was known as one of the most notorious and feared pre-trial prisons (many were sent to Patarei Prison* in Tallinn following their time here). 

*Patarei Prison has now, as of the end of last year, been shut down for visiting

 Walking along Pikk Street...

Walking along Pikk Street...

Continuing down Pikk, head a little further up to Börsi käik, a small, outdoor passageway that gives a quick (and amusing) history of Estonia. This small passageway was named for the Stock Exchange Committee that operated in the nearby Great Guild Hall. According to Rick Steve’s walking tour of Tallinn, during German rule of Estonia, Estonians were demoted to practically a serf status, ruled and demanded to follow orders of the German merchants. The wealthy, Wall Street-esque big shots at the time were members of the Great Guild and basically formed their own fraternity in these halls.

 Börsi käik passageway

Börsi käik passageway

 The entrance to the Great Guild Hall

The entrance to the Great Guild Hall

Across the street from the Great Guild Hall, you will see Maiasmokk, which is the city’s oldest running cafe. It was opened in 1864 (although there was already a cafe & bakery running in the same location from 1806) and was popular with the Soviet soldiers back in the 1900s. If the stories hold true, this cafe is the home to marzipan, made famous by the Baltic German confectioner Georg Stude. The cafe houses its own marzipan museum, and although I can’t speak for the museum, I can tell you the marzipan (...and Irish Coffee) is definitely worth the stop. 

After scheduling your next dentist appointment, walk down a small bit to the fork and look towards the white church on your left (Church of the Holy Spirit). This 13th century church is where the first sermons were given in Estonian post-Reformation. The inside of the church is an intricate, wood-carved interior that can’t be missed. On the outside, you will notice an ornate clock, which is said to be the most photographed thing in Tallinn. The first book published in Estonian was written by the pastor of this church Johann Koell in 1535. 

 The 17th-century clock on the outside of the church

The 17th-century clock on the outside of the church

Old Town Tallinn

From here, turn left down the small street in front of the church (shown above) and head towards the town square (Raekoja plats). On your left when you enter the square, you will see a pharmacy, which claims to be the oldest in Europe, dating from 1422. In this square is where the annual Christmas tree puts up, which Estonians say we can thank them for that tradition. The legend goes that the first Christmas tree was brought to Tallinn in 1441, making it the first Christmas tree to be placed in a town square in Europe. (Latvians dispute this claim, but Estonians give credit to the Latvians for being the ones to first decorate a Christmas tree….there’s a lot of brotherly love/hate between the two countries). The Christmas tree carrying ceremony has become quite an event over the centuries, even bringing Peter the Great in town for it in 1711. Today, Tallinn’s Christmas Market is consistently ranked one of the top markets in Europe. And, I mean, you do have a better chance of meeting the real Santa, since he’s from Finland and doesn’t have far to travel…ya know…

 They love Christmas so much, the tree didn't come down until February 11th this year!! :D 

They love Christmas so much, the tree didn't come down until February 11th this year!! :D 

Raekoja plats

Opposite where you entered the town square you will see the Town Hall, the oldest town hall in the Baltic & Nordic region. Construction started in the 13th century and has been on the UNESCO World Heritage Sites list since 1997, along with the town square. On top of the town hall you will see a weather vane, which just happens to be my favorite local legend. Old Thomas, who watches over the city, is said to have been placed there in honor of a poor boy who stole the hearts of all Tallinn-inians (okay, so does someone have a better word for a Tallinn resident?!). Our hero, little Thomas, was watching a medieval sporting competition that was only open for boys from noble families. On the day Thomas was watching, none of the boys were able to hit the target, so being egged on by his friends, he decided to jump in the competition and won. Since he was from a low birth rank, he wasn’t eligible for the prizes and instead was presented with lifelong employment as a part of the city guard. When he was older, he took part in the Livonian War and secured his status as local hero. When he died, the weather vane was installed in his honor to always look over the city. 

 Tallinn's Town Hall

Tallinn's Town Hall

If that story isn’t heart warming enough, let’s move to a small, circular stone marked with a compass rose in the square. It’s hard to find — and I definitely wouldn’t recommend looking for it during Christmas market season ;) — but hey, if you’re traveling with kids, this is a fun scavenger hunt! If you find the compass rose, you will not only be able to see all 5 towers of Tallinn (one is located through a strategically placed circular hole), but you will also be standing on the end of the Baltic Way, the human chain of freedom. On the 23rd of August in 1989, two million people held hands to form a human chain in peaceful protestation against the Soviet government. I wrote about it and its start in my blog post on Lithuania, but this is (purportedly) where the last person in the human chain was standing. 

If you’re standing in the middle of the square looking towards the town hall, head to your back left, down a small alleyway named Apteegi. At the end of Apteegi, make a left then a quick right down one of the most picturesque streets in Tallinn, Katariina käik. St. Catherine’s Passage is home to St. Catherine's Guild, a collection of craft workshops that use traditional methods for their artwork. On the left side you will see giant, ancient tombstones (some dating back to the 14th century) that used to line the inside of the sanctuary, when the church was still here. At the end of the passage, you will see a cafe called Kohvik Sinilind, my favorite spot in town for some mulled wine. The door gets kind of stuck, so don’t feel awkward if you really need to push on it!

 Inside Sinilind 

Inside Sinilind 

From here, turn right up Müürivahe. If you’re there during any season besides dead of winter, you will see a lot of artist booths set up with Estonian knitted works and the tourist-made famous “Sweater Wall”. No explanation needed. Continue making your way to Viru Gate, part of the defense system of the Tallinn city wall. Turn right up Viru, walking back in the direction of the main square. At the fork stay to your left, then walk to the left around the backside of the Town Hall. This street, Raekoja, is notably the smallest in Estonia. At the end of the street, so about 1.5 seconds later, take a right then a quick left up Dunkri

 This clearly is not considered "dead of winter" in Estonian standards. 

This clearly is not considered "dead of winter" in Estonian standards. 

At the top of Dunkri, you will run into the Cat’s Well. A lot of Finns complain about the water quality in Estonia (actually, a lot refuse to even drink it), but at least they didn’t have to put up with water during medieval days! Supposedly, the water was so bad, that the town residents decided that there must be an evil spirit living in the well, since it was one of the main sources of water for the town. To keep the spirit happy, the locals decided to start making animal sacrifices to the well. When they could, they would throw down cattle or sheep carcasses to the spirit, but usually they ended up just throwing stray cats. It occurred so often, the name stuck. The water never ran dry, but for oh-so mysterious reasons the water quality never cleared up, so the animal sacrificing business stopped in the 19th century. 

 RIP Whiskers and Mittens

RIP Whiskers and Mittens

If you look to the left of the well, you will see the Devil’s Inn, located at Rataskaevu 16, which just happens to be the best rated restaurant in Tallinn. I have taken the ferry to Tallinn just to eat lunch here. Once…or twice. Okay, okay, three times! If you look up above the cozy, brick lined building on the bottom, you will see the window to the room where, folklore has it, the Devil had his wedding. The story I was told was that one night, the innkeeper, after a long winter with no customers, was so depressed he decided it was time to end his life. Just as he was getting the preparations together, there was a knock at the door with a man in a dark cloak. The man offered him a large sum of money if he could have the top floor for a party, with no questions asked on who comes and goes, and no disturbances. The man, in his fitful state, agreed instantly. Later that evening, the top floor was filled with guests and it was so loud the party could be heard up and down the street. The innkeeper’s curiosity got the best of him and he decided to peek in through the keyhole, where he saw two people being wed. The hotel fell silent and then people started suddenly falling ill and dying…

Now, head back to your left, past Dunkri, and you will come to another large church, St. Nicholas’ Church. This large church is a 13th-century Gothic church that served the German merchants and knights. The church was partially destroyed during the Soviet bombing of Tallinn during WWII, but was renovated and now houses an art museum. 

If you’re a beer fan, across the street is a bar called Põrgu. This bar is well-known by Estonian beer lovers for being one of the few places you can get your hands on a pint of Pihtla. Pihtla is a homemade beer made by a man living on an Estonian island about two hours away from Tallinn. He only produces a certain amount each year and refuses to be commercialized, instead serving a few locations throughout Estonia. 

From the church, or the bar, head back the way you came, but instead turn left on Lühike jalg. If you’re looking for artistic souvenirs, the shop at the corner of Lühike jalg and Rüütli is one of my favorites in Tallinn. They always have a great collection of eccentric mugs and housewares. Walk up Short Leg Lane, making your way to the top of the stairs. Look at the large oak door on your left: during medieval times, this was the one of the gates at the wall separating the two cities (between the lower class and the upper class). Because Estonians love their rituals and history, this passage is still used as a meeting point for the mayor of Tallinn and the Prime Minister whenever there is an agreement made between the city and the country. 

Lühike jalg
 Winding up Lühike jalg

Winding up Lühike jalg

But, don’t go through the cobbled passage, instead, go straight through the white arch and make your way into the Danish King’s Garden. This is the spot where the Danes insist that a white cross fell from heaven, landing in a pool of blood as Danish spirit was waning. It inspired them to keep fighting, leading to a victory over the Estonians. The Short Leg Gate Tower leading out from the garden on the right is infamous as the most haunted place in Tallinn. There have been reports of an executed black monk, a lion, and a galleon floating through the wall. In medieval times, the gate was locked each night to keep the common people out, but mainly to keep the ghosts away from the nobility. 

 Tallinn at night from the King's Garden

Tallinn at night from the King's Garden

 Inside the garden

Inside the garden

 Even though it seems I only go to Tallinn in the winter, it's just as lovely during the summertime :)

Even though it seems I only go to Tallinn in the winter, it's just as lovely during the summertime :)

The Maiden Tower (if you’re standing in the garden with the city behind you, it’s to the left of the Short Leg Gate) was actually once used as prison for prostitutes. Yes, we have another story folks: a deal was made between an ugly prostitute and the Devil (we both seem to have a love for Tallinn in common), she could gain beauty if he got her soul. But, with a caveat. The girl had to entice as many men townsfolk to come to her as she could. In the end, the was declared a witch by the townsfolk and executed. You can climb up the small, winding stairs (hey, St. Olav’s Church was just a practice round) to the Maiden Tower, where you can visit the cafe. They have outdoor seating and if you continue past the counter, a cozy attic room for lounging about and ghost spotting. 

 Up at the Maiden's Tower

Up at the Maiden's Tower

Underneath the garden and the Kiek de Kok (an artillery tower from 1475), you can take a tour of the well-preserved 17th-century tunnels. During those times, Estonia was part of the Swedish empire and Sweden built the tunnels to shelter soldiers and ammunition, and to spy on the enemy (primarily Russia). The tunnels were hardly used, but they did come in handy during WWII when they were reused as bomb shelters. 

 Outside of Kiek de Kok

Outside of Kiek de Kok

If you feel like seeing a something a little more racy during your tour, walk through the Short Leg Tower Gate towards the Kiek de Kok and find Adam and Eve’s 50-Shades-of-Grey-Limestone. The religiously inspired monument is quite ironic for it’s extremely sexual vibe…

From here, head towards the grand St. Alexander Nevsky Cathedral standing in front of you. It was completed in 1900, in a Russian Revival architectural style, when Estonia was part of the tsarist empire. This cathedral was immediately looked upon in disdain by Estonians; not just because of the symbol of oppression under Russian rule, but also due to the fact that an Estonian folk hero, Kalev, is said to be buried on the ground beneath the it. Estonians despised it so much it was actually scheduled for demolition in 1924 (which is saying a lot, when so many other buildings from centuries of Danish, Swedish, and German rule were left intact), but never occurred due to lack of funds. I don’t usually care for construction materials, but the base of the building is Finnish granite (Finland gained independence from Russia in 1917). Make sure to go inside to see the beautiful mosaics and altars. 

 St Alexander Nevsky Cathderal

St Alexander Nevsky Cathderal

After exiting the cathedral, look across the street at the can’t-miss Pepto-bismol building. This is an 18th-century Baroque addition to the Toompea Castle. Per Estonian mythology, the wife (Linda) of our Estonian hero above (Kalev) built the entire hill that Toompea sits on with her bare hands. She mourned his death and built the hill in honor of him. (And now you’re starting to see why Estonians really can’t stand the Russian cathedral looming there). Sometimes, this area is referred to as “Lindanise” in Estonian. The castle has been in use since at least the 9th century. Nowadays, the castle is home to the Estonian Parliament, Riigikogu. Outside of Riigikogu, you can see the two Estonian flags flying: the flag of the first republic, from 1918-1940, and the flag of the second, present day republic (1991-present). Two independence days are still celebrated in Estonia, the day of 1918 and the day of 1991, as Estonians claim they were always independent, just went through some occupation periods (by the Soviets, then the Nazis, then back to the Soviets).  

 Riigikogu

Riigikogu

From the parliament building, work your way up Toom Kooli to the Dome Church. This is the oldest standing church in Tallinn (and in mainland Estonia), first being mentioned in 1233. Inside, the floors have tombstones dating back to the 13th century. Swedish King Johann III's daughter, Sophia Gyllenhelm, is buried here, along with other Swedish and Russian military members. During atheist Soviet rule, this church was supposedly used as a martial arts training center. 

 St. Mary's Cathedral (Dome Church)

St. Mary's Cathedral (Dome Church)

After exploring the Dome Church, backtrack towards Toompea Castle, turning right on Toom-Kooli before getting to the castle. Walk down the street towards the Canadian Embassy, turn left at the end of the street, turn right to curve your way around the building and the theatre, then walk down and along the path of the city wall. The oldest sections of Tallinn's city wall were built in the 13th century, where you will be walking now. Over the course of the next three centuries, this wall became one of the largest and strongest defense systems in all of Northern Europe. More than half of the wall has been preserved, leaving 1.85 km of the wall remaining. Back in its prime, the wall was three meters thick, sixteen meters high, and four kilometers long with 46 defense towers located along it. Walk down the city wall until you see stairs, where you can make your way up to the Patkuli Viewpoint.

 Walking along the city wall

Walking along the city wall

Toompea Castle.jpg

From here you get a great view of Old Town, where you can see the St. Olav’s Church. In the courtyard, don’t miss out on buying some sweet almonds from the ladies dressed up in traditional clothing. They’re delicious and they’re cheap, so who cares if it looks like a tourist trap. They trap me, every time. 

 Viewpoint from Patkuli

Viewpoint from Patkuli

After the first viewpoint, make your way through the arch on the other side of the courtyard, turn immediately left, follow the road to the right, take your first left again, and make your way to Kohtuotsa Viewpoint. This gives a similar view as Patkuli, but you can also see the Viru area of Tallinn, just outside of Old Town. Hotel Viru was formerly home to the KGB’s espionage unit and you can now tour it as it once was during its communist hold (tour reservations must be made in advance). 

 Looking from the viewpoint towards Hotel Viru

Looking from the viewpoint towards Hotel Viru

After the viewpoint, you can meander back towards the Town Square, or go explore another part of Tallinn (I highly recommend Kalamaja and Kadriorg)! 

I hope you enjoy Tallinn and it captures your heart as much as it did mine! Xoxo