Top 15 Things To Do In Tallinn Old Town, Estonia

Updated on May 6th, 2024

Here is my guide to the top 15 things to do in Tallinn Old Town in Estonia. If you are looking for a glimpse into life in medieval times then look no further for a good value & beautiful European city.”

Where?

Old Town, Tallinn, Estonia

Why?

I had heard that Tallinn was a beautiful & magical city. I was looking for the perfect location for a short getaway in November & read a few articles that said this is the time to visit. Tallinn is one of the oldest capital cities in Northern Europe & the Old Town is one of the best-preserved medieval town centres in the world. One of the main reasons to visit at this time is the Christmas Market so having checked the dates, it all fitted together perfectly!

When to visit?

I went in November when it was very cold (-6ºC at worst). They had just had the first snow of the season when I arrived at the end of the month. I left in the first week of December to a torrential snow flurry which slowed down our take off. The nights were longer & the days short which was actually better to see the giant Christmas Tree in the Town Square & made it feel more magical. The streets were almost empty & few tourists were there to get in the way. The light seemed to be always dusk so when the sun was out the vistas were spectacular.

The downside was that the weather was cold, so it was hard to do everything all at once without a regular warm-up in a café, bar, restaurant or shop. I believe that it’s possible to see Tallinn in a day, but why would you want to rush it?

Talking to locals they say summer is so busy that it’s hard to walk down the streets & actually get anywhere.

At one time there can be up to 6 cruise ships docked, & everyone only has 4 hours, so never leave the Old Town. In 2019 there is a big folk festival (it happens every 5 years) which has choirs (some up to 30,000 strong!) & traditional singing & dancing.”

It would be great to visit as it sounds like such a spectacle. Days are long as it’s the time for “White Nights”.

The other alternative is September which we heard was quieter from a tourist perspective but a warmer climate. Basically, take your pick & whenever you go, I think you will find the Old Town magical.

What are my Top 15 Things to Do in Tallinn Old Town?

The beauty of Tallinn Old Town is all around & it’s small enough that within a couple of days, you can get to know the labyrinthine streets pretty well. I am not keen to rush these things so spent a week here with a couple of days excursion to Helsinki. Here are my Top Picks:

Great Coast Gate

This was my first introduction to the Old Town as it was the entrance from my Airbnb. It was an impressive place to start as it’s one of the best-preserved of all the gates, especially considering it dates from before 1400. The outside bears a carving of the Tallinn coat of arms, and the inside has a crucifix.

St Olaf’s Church

This is the landmark which can be seen throughout the town. Despite that, it’s still hard to believe that for a time in the 16th Century, this was one of the tallest buildings in the world. Apparently, you can get a great view if you can bear the claustrophobia-inducing staircase up to the top of the tower. I didn’t partake but it’s well worth stopping by just to view night or day!

Town Hall Square (Raekoja Plats)

In the centre of the Old Town, all roads lead to this spectacular square. One side is filled with the impressive Gothic Town Hall, the only surviving one in Northern Europe. Overlooking proceedings is the tower which houses Old Thomas (Vana Toomas) which is the symbol & guardian of the city. Again, apparently, you can climb the tower for views. Once again I chose to admire from outside on the ground!

On the other sides of the square are a gorgeous collection of coloured houses, all dating between the 15th & 17th Centuries. You’re also never short of a café or restaurant in the area.

St Catherine’s Passage (Katariina Kaik)

Probably the most beautiful alleyway in the whole town & feels like you’ve stepped back into medieval Tallinn. Along the walls to the entrance are some huge tombstones which are from the St Catherine’s Dominican Friary.

They set the scene before you walk through the ancient archways & stop in the alcoves to take in the experience.”

Along here is also a collection of boutiques offering locally produced ceramics & textiles for you to buy should you be that way inclined!

Long Leg Gate

On my second stay, I was literally in an Airbnb apartment just behind this landmark & was pretty blown away by it. I guess in the whole scheme of things & the medieval gorgeousness of Tallinn generally it may look a tiny bit unimpressive. However, it is also the entrance & a great route up the cobbled hill which leads to….

Toompea Castle

You can’t visit without a trip to the parliament building. In the case of Estonia, this is a pink baroque building that was converted by the Russians, and overseen by Catherine the Great. At the back, though you can still view a remnant of its original structure in the shape of Pikk Hermann, a 14th Century hilltop castle tower.

Alexander Nevsky Orthodox Cathedral.

This sits opposite Toompea Castle & is a Russian-built onion-domed addition to the skyline, built in 1900. No cameras are allowed inside but outside makes an impressive photo opportunity!

Viewpoints

Up the hill, as you walk from the Castle are 2 spots where you can get a view & your bearings of this beautiful Old Town. Patkul Lookout (Patkuli Vaateplats) gives you a vantage point from which you can see the towers & spires in all their glory with a backdrop of the sea. Not far away is Court Square Lookout (Kohtuotsa Vaateplats) which is the same view but with less sea & I think a better view of the Tallinn Old Town as a whole. These are where you can take photos of those archetypal Tallinn views that you see everywhere. Enjoy, & if you’re lucky you may get to meet one of the Tallinn residents, the very friendly & enormous seagulls!

Kiek in de Kök

My favourite part of the wall, conjuring up visions of medieval times in Toompea. Here is the location of one of Tallinn’s most impressive cannon towers which now houses a part of the City Museum.

Apparently, the towers were severely damaged during one of the wars & several of Ivan the Terrible’s cannonballs still remain in the walls!”

Through the archway is a small square whose atmospheric views are made even eerier by the addition of a number of bronze statues of monks.

Visit a Café

These are all over the city so you’re never short of somewhere to stop for a while for a coffee, hot chocolate & my personal favourite, Glögg (hot wine!). My recommendation is Maiasmokk. Opened in 1864, it is one of the oldest cafes in Tallinn. This place is famed for its impressive window displays (a moving Ferris wheel) & marzipan figures. Please go & have a look inside the Marzipan Room where you can see displays of the characters & witness the artists who create them at work.

Hot Wine

I have mentioned this a few times already but did a bit of a study while in Tallinn! Basically, this is red wine, heated with nuts & dried fruits added. What’s not to love?! If you see signs for Glögg, Glögi or Hoogvein, then it’s hard to go wrong. Some are also made of Vana Tallinn, the local spirit which is a bit sweeter but well worth a try.

Visit a Bar

Tallinn has gained a reputation for being a party town, fuelled by cheaper alcohol prices & late-night opening (at least 2am). The main area is situated around the triangle of streets bordered by the city walls, Viru & Suur-Karja. It’s worth a visit & there seems to be something for everyone in the area. Going in wintertime meant that many bars were much less busy than they would be in the summer. Particularly on a Sunday, it looks like a totally different place to a Saturday night. If you want to see the place in full swing, then head there during the weekend. For a bit more space & better service, try a weekday. I tried the following during my time:

• Labor Baar – gimmicky but worth a visit if you fancy taking your drinks from test tubes or scientific beakers! Interesting décor & light sensor tables.
• Sigmund Freud Bar – I was told they did the best cocktails in Tallinn. I tried a few, they were delicious & very creative.

Christmas Markets

While I was there, the Town Square was home to the pretty Christmas markets (open from mid-Nov – 1st week in Jan). The centrepiece was the Christmas Tree which was first erected in the square in 1441, making it one of the earliest recorded decorated trees in the yuletide season. It was the first Christmas Tree ever put on display in Europe. Surely that makes it worth a visit in the cold?! If you brave it, almost every stall is very willing to sell you Glögg of various descriptions to help you warm up!

Eat Local

For me, this was the biggest surprise on my visit to Tallinn. I wasn’t sure what to expect from the food but honestly enjoyed everything I ate! As well as Estonian dishes, there are Russian & Nordic influences to the cuisine & all I can do is encourage you to embrace the whole culinary experience.

 One thing to note is that many of the restaurants are located below ground, down a set of stairs. In winter, because of the climate, many have doors closed & can look a little uninviting. Persist & you will be rewarded!”

Some of my favourites were:

• Odessa – Ukranian Restaurant below ground but with delicious food & excellent service. We were given a complimentary horseradish vodka which was a great place to start & delicious!
• Trofe – Again below ground but this time a Nordic Restaurant. I tried Roe Deer Cutlet & my friend had the most enormous venison burger. Hearty & gorgeous food!
• Rataskaevu 16 – This is the top-rated restaurant in Tallinn on Trip Advisor. I found it as it was just around the corner & -6ºC! Whatever you feel about TripAdvisor (& I mainly take everything with a pinch of salt), this is a great restaurant. The service was exceptional & the food delicious (although not the huge portions you may get elsewhere). The braised elk is apparently the house speciality & I thoroughly enjoyed it!
• Kaerjaan – Modern Estonian, right on Town Hall Square. Great location & delicious food. I tried the Lake Peipus Zander (I had to check beforehand if that meant fish!)

Walk

You may agree or disagree with the choices I have made here but my biggest advice is just WALK. Every step you take and corner you turn on these medieval cobbles is a joy & like a step back in time. You can turn off the main road & literally feel like you have just arrived in the 16th Century. Whatever you do & wherever you go in the magical Old Town of Tallinn is special. Just Walk & Enjoy!

Where to stay?

Booking.com

If you enjoyed this post from Eastern Europe, here a some other videos of my further adventures in this fascinating region.

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