Tallinn Old Town, Estonia’s Medieval Fairytale City

Did you know that the Estonian capital is a fairytale city with hundreds of years of history and traditions? The thick walls surrounding Tallinn Old Town have seen many different rulers but always protected the city and helped to retain it as it was.

I spent a winter weekend in the UNESCO listed Old Town of Tallinn, strolling its cobbled streets and trying to imagine what its gabled houses have seen in the thousand years since the city was founded.

This post will show you the historic Tallinn Old Town and a walking itinerary to explore the most beautiful parts of it.

Historic Tallinn Old Town: city wall, towers and red roofs

Tallinn, the Capital of Estonia

Estonia is a small country and best known for its capital where 450,000, one third of the total population live.

Tallinn is located on the south coast of the Gulf of Finland, just across from Helsinki. Both Helsinki and Tallinn have good international flight connections and the two cities are linked by frequent daily ferries. The journey takes 2,5 hours.

Tallinn’s new town has glassed skyscrapers, fancy shopping malls, new great museums, and those huge suburbs built under the Soviet rule. The new town is constantly changing and developing but there’s something that remains the same, the Old Town.

Typical medieval street in Tallinn Old Town

Tallinn Old Town Walking Itinerary

As most of Tallinn Old Town is a car-free zone, walking is the way to explore it. The historic center is easy to walk through, provided you have proper shoes.

This is Tallinn Old Town on the map. Zoom out the map to see where Tallinn is located, and zoom in to see the Old Town in detail.

Tallinn Old Town Walking Map

When you visit Tallinn, the Old Town is the first place to go to, it’s where most sights are. There is an upper town on the hill and a lower town below, and the whole has a medieval town wall around it, with many fine towers. The upper town was for the rulers and the lower town for the citizens.

Both areas are equally beautiful but we will start from the lower town.

Around Town Hall Square

Sunday afternoon around Tallinn Town Hall Square (Raekoja Plats)

As the Old Town of Tallinn has those thick stone walls around it you have to look for a gate through which to enter. The most common gate to enter is Viru Gate from the new town, followed by Viru Street, the widest and busiest of all old town streets.

The cobbled Town Hall Square (Raekoja Plats) has fantastic old buildings on all four sides. This is the local meeting point and the heart of the city. In summer open-air cafes fill the square and in winter the square has a Christmas market and most restaurants only serve indoors.

Yet some tables are out in winter as well. This tiny cafe puts out its tables in the town hall arcade.

Sitting out for glögg on Tallin Raekoja Plats

Viru Street from Viru Gate to the heart of the Old Town

Talllinn Old Town restaurants: Olde Hansa

Tallinn Vana Turg

Tallinn Old Town restaurants: Peppersack

Traditional Estonian Restaurant Kuldse Notsu Korts

Walking around the Lower Town

Tallinn Old Town’s architecture has many layers

Tallinn’s lower town has a Hanseatic background. In the Hanseatic league’s days of glory Tallinn was one of the principal trading cities in the Baltic area, along with Lubeck, Stockholm and Riga. That was in the 14th to 16th centuries. Today Tallinn still is full of fine buildings from to those days, buildings like the Great Guild Hall on Suurgildi plats. However, there have been other influences as well.

First came the Danes that gave the city its name. The name Tallinn refers to the Estonian ‘Danish town’. Then after the Hanseatic league came the Swedes and Russians, and all these periods have made the city what it is.

Tallinn has a long cafe culture and the Estonians claim they invented marzipan. This is one of Tallinn’s oldest confectioneries, Maiasmokk Marzipan Room:

Marzipan cafe Maiasmokk and Tallinn’s Great Guild Hall

Medieval Tallinn: Puhavaimu Street

Cafe restaurant on the Long Leg Street

Medieval beauty

Work continues and towns never get ready

Before Estonia got an independent country the Russians were the last people to rule here. In the Soviet years people moved to the new suburbs and the Old Town was not the thing. Then a massive renovation started in the 1990’s and it’s all done, almost. This house is an exception but I kind of like the way it looks.

The Estonians are really doing a great job, They recreated Tallinn Old Town to be the purest medieval old town in Northern Europe. Tallinn really is a fairytale town.

Toompea Hill

Neitsitoorn, Toompea HIll

Tallinn’s 2 km town wall winds it way to the upper town Toompea Hill. Half of the wall’s original 46 towers still stand there and a couple of them are serving as museums. Some of the towers you can climb and in places the wall has a walkway at the top.

Toompea Hill is the place Tallinn and Estonia is ruled from. It began with the Danes who came and built their mighty stone castle on the hill. The castle still stands there, in original condition after 800 years. You can best spot the castle from behind the hill. From the hill itself you can only see the pink Baroque part of it, the Estonian Parliament building.

Toompea Hill contains many important buildings like cathedrals, government offices and embassies, and a hidden lookout at the north end.

Tallinn skyline from Patkuli lookout

The Dome of Tallinn, built by the Danes in 1240

The Dome St Mary the Virgin and Estonian flags

View of Toompea, the upper town of Tallinn

Then there is the amazing, huge Russian Orthodox church, Alexander Nevsky Cathedral. A Russian tsar built it after a fight, putting it on the Estonian national hero Kalev’s grave.

The cathedral has much decoration both inside and out. The inside is shining with gold and has beautiful icons, but despite that the Estonians thought about tearing the building down after independence. Here it stands, however, and is one of the most stunning landmarks of Tallinn.

Tallinn’s Alexander Nevsky Cathedral

Estonian Parliament building at the top of Tallinn Old Town

Red roofs seen from Toompea Hill

Tallinn city wall and towers backed by the Baltic Sea

Tallinn souvenirs

Onion domes of Alexander Nevsky Cathedral

More Tallinn Old Town Sights

Tallinn lower town has many nice shops

Our Tallinn walk now goes back to the lower town. To get down we will take the Long Leg Street (Pikk jalg). It’s Tallinn’s oldest street, all the way from the Viking times.

The other link between Toompea and the lower town is Short Leg Street (Luhike jalk). If you use my Tallinn walking map you will take the Short Leg up and the Long Leg down. Both streets have an arch through the town wall, and more arches will follow in the lower town.

Tallinn Old Town has arches and tunnels

Munga Kelder, one more old town restaurant

Katarina Käik, St Catherine’s Passageway

Katariina Kaik passageway, Tallinn Old Town

This is where you get through the white arch: St Catherine’s Passageway. It belongs to Tallinn’s oldest streets, cobbled, narrow, lined with crafts and arts workshops on one side. The other side again has gravestones and ruins of an old wall.

That was Tallinn’s biggest church that somehow disappeared and only some graves are left. Not many Tallinn Old Town buildings have disappeared with time but this is one of them.

St Catherine’s church gravestones along Katarina Käik passageway

Climbing Tallinn Town Wall

Tallinn town wall and Estonian knitwear

We will soon be back to Viru Gate where we started. Here is the city wall again and stalls selling wool wear very much needed in the Estonian winter. Pure wool at very reasonable prices, maybe Christmas presents for friends and family?

Traditional Estonian wool sweaters

Back in the street is Hellemann Tower, the best city wall tower to climb. Pay a small fee, take the spiral stairs up and walk a 200 m section of the town wall. This is a fantastic place for a bird’s eye view of both the Old Town and the new city, at a close distance compared to the Toompea view.

The tower itself has an art gallery, but since the 14th century when the tower was built it has been a prison and a weapons store as well.

Views from Hellemann Tower:

Hellemann Tower walkway, Tallinn Old Town

Tallinn roofs from the medieval town wall

Looking out from a prison cell

The old town wall surrounding Tallinn

My Tallinn walk ends here, we have seen the main sights. If you are on a one day trip you must be getting back to the ferry or airport by now. However if you stay the evening in Tallinn, go and see what it looks like after dark.

To end my post, some samples of the enchanting, historic city of Tallinn: