Day 297: Exploring Medieval Tallinn

Weather Update: Sunshine. High 23c

Elevation: 12 Metres. 39 Ft

Starting the Day

First thing: local SIM card, €4 for a week. Pizza slice for breakfast, and up, up, and away we go. First stop was Viru Gate, only a five-minute walk from the Imaginary Hostel.

Viru Gate

At one time, there were 45 towers built into the walls that protected Tallinn. Remarkably, 26 of those remain, even though during World War II the Russian army bombed the city. Two of the best preserved are called the Viru Gate.

For many years, the two towers were covered in ivy, which protected them from the elements. When you enter Old Town from the bus station, it really is like stepping back in time.

The Barbican of Viru Gate was part of the defence system of Tallinn’s city wall, built in the 14th century. A couple of centuries later, the city had eight gates consisting of several towers and curtain walls connecting them. The main tower of a gate was always square, and the barbicans were equipped with one or two small round towers.

As the entrances to Old Town were widened, several gates were demolished. The Viru Gate itself was partly removed to make way for a horse-drawn tram route that once connected the Old Market with Kadriorg. However, the corner towers were preserved. You can also still see part of the bastion called Musumägi. Today, Viru Street, with its many shops and restaurants, is one of the busiest pedestrian streets in Old Town.

Tallinn Town Hall

From Viru Gate, I moved on toward the Town Hall. All the sites in Tallinn are within easy walking distance, which makes exploring straightforward.

Along the way, I stopped to photograph a nice building. Just like that, three people stepped in front of me, striking poses as if they were movie stars, without a care in the world. I waited patiently for ten minutes until they moved, then finally snapped my photo (The Olde Hansa).

A short walk further brought me to Tallinn Town Hall, the oldest and only preserved Gothic-style city hall in Northern Europe.

First mentioned in 1322, the building’s history goes back to the 13th century. Completed in its current form in 1404, it has served many functions. Today, it is a ceremonial building for the city government, but for centuries, it was also a courthouse. Inside, magnificent Gothic arches, wood carvings, tapestries, and paintings reflect the wealth of a Hanseatic town. The works of art even reminded aldermen of fair judgment when presiding over cases.

Sadly, the building is closed to the public, so I could only admire it from the outside.

St. Nicholas Church

Just around the corner, within another short walk, stood St. Nicholas Church. Unfortunately, it was closed at first, but when I returned later, I discovered that despite some online sources suggesting free entry, it now charges €15 (NZD 29.85) as it operates as a museum.

I had only wanted to see the church architecture itself, not the museum exhibits, so I decided not to go in.

The Old Town’s St. Nicholas Church is a late Gothic, early Baroque structure built between 1732–1737 on the site of a former 13th-century church, also dedicated to Saint Nicholas—the patron of fishermen and sailors. Originally Catholic, it became Lutheran during the Protestant Reformation in the 1520s.

It was partially destroyed in the Soviet bombing of Tallinn during World War II, but later restored. Since then, it has not been used for regular worship but instead houses much of the surviving medieval artwork of Tallinn.

Bastion Tunnels & Kiek in de Kök

Leaving the church, I made my way uphill toward the Bastion Tunnels. The artillery tower here is called Kiek in de Kök, meaning “Peep into the Kitchen” in German. Occupants of the tower could look down into the kitchens of nearby homes—hence the name.

I decided to pay the entry fee (with a senior discount), and it was well worth it. Standing on those fortifications, I could almost feel the presence of the soldiers and warriors who defended Tallinn across the centuries. I walked the ramparts, climbed the tower, and browsed the small museum before enjoying a coffee in its café.

The tunnels themselves are fascinating. Built in the 17th and 18th centuries, they allowed soldiers to move unseen, transporting ammunition and monitoring enemy attempts to dig mines. As cannons became standard in warfare, fortifications changed—walls became lower and wider, supported by earthworks that could absorb cannon fire. The Ingrian and Swedish bastions were part of a colossal fortification plan devised by Eric Dahlberg, a Swedish military engineer.

By 1857, the fortifications were no longer used for military purposes, and parks were established on the bastion tops.

Toompea Castle & Alexander Nevsky Cathedral

Just across the street stood Toompea Castle, perched on Toompea Hill. This medieval fortress is now home to the Estonian Parliament, though access is restricted.

Its history goes back to an ancient stronghold used as early as the 9th century. Denmark’s crusaders captured it in 1219, followed by the Order of the Brethren of the Sword in 1227, who rebuilt and fortified it further.

Across the square rises the striking Alexander Nevsky Cathedral, a richly decorated Orthodox church completed in 1900 during Estonia’s time under Russian rule. Built directly opposite Toompea Castle, its location symbolised Russian supremacy.

Inside, photography is not allowed, but it is free to enter. The mosaics and iconography, along with the ensemble of 11 bells (including Tallinn’s largest at 15 tons), make it truly impressive. During Soviet occupation, the church fell into disrepair, but it has since been beautifully restored.

Pikk Hermann

Around the corner is Pikk Hermann, the southwest tower of Toompea Castle. First built in the 1360s and expanded in the 16th century, it now stands 45.6 meters tall.

The Estonian national flag flies from its top every sunrise, accompanied by the anthem, and is lowered at sunset. On average, 15 flags are used each year, for 420 krooni (€27). In autumn storms, a flag might last only a day, while in summer it could endure for weeks. Damaged flags were often repaired to save money.

St. Mary’s Church

Heading back downhill, I passed St. Mary’s Church. Sadly, this is another case where the building now functions as a museum rather than a church. The warden even told me, “God does not live here.”

Entry fees were charged, and photography cost €3, so I chose not to go in.

Leaving St. Mary’s Church, I continued downhill toward the Town Hall, passing through a gate with a curious name: The Long Leg Gate, which separates the Upper Town from the Lower Town.

Long Leg Gate

Walking through, I could almost picture the chaos of centuries past. During the time of the Danish Order, transport here was mostly on horseback. Later, under Swedish rule, horse and carriages became more common, and the steep descent made this one of the trickiest stretches in the city. The road was widened and levelled at the end of the 18th century, but still coachmen had to call out “CAUTION!” as they descended, since the gate led straight into a sharp curve and three busy intersecting streets. Accidents were frequent, and some tragically fatal.

The first version of the road didn’t even have a gate. One was later added, and soon a wooden tower was built above it so watchmen could keep a closer eye on the traffic. It’s easy to imagine them standing above, scanning for trouble.

The Long Leg Gate also reminds me that the Upper and Lower Towns were not always on friendly terms. The defensive wall along Long Leg Street, finished in the 15th century, was even called “the wall of mistrust.” Passing through it today, I felt the weight of that history—how one city could be divided by suspicion even within its own walls.

Checking in – Zinc Old Town Hostel

My final stop was checking into the Zinc Old Town Hostel. The front desk staff weren’t very sociable (as other reviews also noted), but the facilities themselves were good: well-kept showers and toilets, laundry for €4 (much cheaper than the €10 at Imaginary Hostel), and my room was spacious with a table, chairs, and even a sofa.

Wrapping Up the Day

Wow, I got through a lot today—11.77 km in total. A good workout, and much needed after sitting around in Poland eating and drinking!

On the way, I met Remy from France, who’s heading to Riga. I signed him up for the blog, and I know he is going to Riga and the Cinnamon Sally Hostel and gave him directions—he’ll really enjoy it there.

That’s it for today. More to come tomorrow, but for now, sleep calls.

Take care, fellow travellers following along with me. And if you’re sitting at home watching TV—well, there’s no harm in that either.

—Andrew

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