Estonia Europe

Old Town Tallinn – What to Do in Estonia’s Medieval City

Old Town, Tallinn, Estonia

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5 minutes in the Old Town of Tallinn, Estonia was all it took for me to fall in love with the city. The city is so quaint and charming. Surrounded by the remnants of an old city wall, Tallinn is an old medieval city made up of quaint alleyways and cobblestone streets. I spent 2 days wandering through old town Tallinn, Estonia and was impressed by how much there was to see. The old town itself is a pretty small area, but there are countless alleyways to wander, shops to explore, and history to take in. The old town is a very walk-able area and no car is needed.

Although the old town in Tallinn, Estonia was my favorite part of the city, it’s definitely worth it to take at least a day to explore the rest of the city outside of the old town city walls. I’ve written a blog on the best things to do outside of the old town to help you get ideas.

Check out the top sights and activities to do in Tallinn:

Hellemann wall and watchtower in Tallinn, Estonia
Hellemann wall and watchtower in Tallinn, Estonia

Walk on the Old City Wall at Hellemann Tower

One of the most charming aspects of Tallinn’s Old Town is the preserved city wall that encircles the city. The first of the city wall’s were built in the 13th century. Over the next few century’s the walls and towers continued to be built and reconstructed. Today, large portions of the city walls and numerous watchtowers are still standing and can be explored. One of the best places to walk on the wall is at Hellemann Tower. From here you can climb inside the tower and up onto the wall. A short stretch of wall is open to be walked on between towers. The wall provides a great view of the city as well as insight into the history of Tallinn and the walls.

Kiek in de Kok Museum in Tallinn
Kiek in de Kok Museum in Tallinn

Learn the Story of Tallinn at Kiek in de Kok Museum

Another top spot to explore the city wall and climb watchtowers is at Kiek in de Kok. This portion of wall is longer than that at Hellemann Tower. Kiek in de Kok is a museum that tells the story of Tallinn’s history. The museum is comprised of multiple underground tunnels and 4 watchtowers. The grounds outside the museum are beautiful and worth spending some time walking through. Behind the museum, the Danish King’s Garden provides a quiet spot to view the towers and wall, and see some green space in the city.

The Viru Gate, entrance into Tallinn Old Town
The Viru Gate, entrance into Tallinn Old Town

Enter Old Town Through the Historic Viru Gate

Viru Gate is the main entrance into the Old Town. It’s an unassuming portion of wall with a space in the middle for people and cars. It’s a small, historically significant area and worth walking through to get a feel for what the old town felt like century’s ago. Outside of the gates is a flower market.

Tallinn Old Town Hall Square
Tallinn Old Town Hall Square

People Watch in Town Hall Square

Located at the center of the old town, the Town Hall Square is one of the liveliest areas of the old town. The square is surrounded by bars and restaurants and will almost always have people sitting outside. It’s a great spot to people watch and relax at a restaurant. While exploring the Old Town many streets and alleyways lead into the square so it’s a place you’ll likely pass through a time or two. The Tallinn Town Hall is also located in the square as well as the Town Hall Pharmacy.

The KGB Prison Cells Museum in Tallinn
The KGB Prison Cells Museum in Tallinn

Tour the KGB Museum and KGB Prison Cells

The KGB Museum and KGB Prison Cells Museum both tell the story of Estonia’s dark history with the Soviet Union. Throughout history the Soviet Union was one of empires that occupied Estonia, most recently from 1944 – 1991, before Estonia’s independence in 1991. The KGB Museum tells the story of the Soviet Occupation of Estonia. The KGB Prison Cells Museum tells the darker story of where Estonian’s were imprisoned under Soviet Control. Both are very interesting, sad, and historical places worth a visit to learn about Estonia’s history while visiting the Old Town.

Some of old town Tallinn's alleyways
Some of old town Tallinn’s alleyways

Wander the Old Towns Many Alleyways

Tallinn’s Old Town is made up of a maze of small streets and alleyways. The alleyways are worth exploring. Many charming shops and restaurants can be found in these small, unassuming alleys. Notable alleys include Katariina Kaik and Meistrite Hoov, but there are so many more throughout the town just waiting to be wandered.

The Alexander Nevsky Cathedral in Old Town, Tallinn, Estonia
The Alexander Nevsky Cathedral in Old Town, Tallinn, Estonia

Visit the Alexander Nevsky Cathedral

Towering over Tallinn’s old town on Toompea Hill sits the Alexander Nevsky Cathedral. The Alexander Nevsky Cathedral is the largest orthodox church in Tallinn and was constructed while Estonia was still under Russian Rule in the late 1800’s. The cathedral’s cupola (domes) can be seen from many different areas in Tallinn. After a short trek up Toompea Hill, you’ll be greeted by this stunning cathedral. Entrance into the cathedral is free.

Traditional Estonia food at Peppersack
Traditional Estonia food at Peppersack

Eat at a Themed Restaurant

Eating at a themed restaurant is definitely touristy, but it’s also fun. The themed restaurants in the Tallinn go all out with costumed waitstaff, olden cuisines, and even mealtime shows. Two of the most popular themed restaurants are Olde Hansa and Peppersack. These restaurants are across the street from each other in the center of the old town. I opted to eat at Peppersack as I thought the menu sounded better at the time. I tried rabbit meatballs and a moose meat cutlet. The servers were all in costume and randomly broke out into a show part way through dinner which I was not expecting. Honestly, the show was kind of weird and I don’t know how it fit in with the restaurant, but it was fun none the less.

View of Tallinn from the Patkuli viewing platform
View of Tallinn from the Patkuli viewing platform

Admire Tallinn from a Viewing Platform

While on Toompea Hill, stop by the two main viewing platforms to get the best views overlooking Tallinn’s Old Town. There are two main viewing platforms upon the hill- Kohtuotsa and Patkuli. From both platforms you get a different view looking out over the old town and because each view is different both platforms are worth a visit. You’ll be able to see the city wall, numerous watchtowers, red-tiled house roofs, and on a clear day the Baltic Sea off in the distance.

Two fun bench statues in Tallinn
Two fun bench statues in Tallinn

Find the Fun Bench Statues for Photo Ops

Spread throughout the Old Town are public benches with statues. These are fun, quirky, a great place to sit for a short rest, and fun to find while out exploring. Some of the benches include a dog and a pig.

Old Town, Tallinn, Estonia
Old Town, Tallinn, Estonia

Where to Stay in Tallinn

Tallinn felt very compact. Both the Old Town and areas outside of Old Town did not take long to get to. For this reason, I would recommend situating yourself in the Old Town and using the tram system to get to and from the sights outside of the old city walls. There are plenty of hotels to choose from in the Tallinn old town. A few great options include:

Hotel Telegraff, Autograph Collection

Merchants House Hotel

My City Hotel, Tallinn

Lai 22 Hostel & Bar

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