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Tallinn: Medieval to Modern

  • Bev Baraka
  • Oct 28, 2023
  • 7 min read

Tallinn in Estonia, is the most Medieval city I have seen - even more than Riga, Latvia. The center is the old walled city which once contained everything - life was contained within. A central courtyard was the meeting place for friends, merchants, and protests.

The old walled city with Gothic towers and medieval style buildings
The old walled city of Tallin, Estonia

Surprisingly, Tallinn is only about 80 km from Helsinki, Finland. But, as I travelled out from Moscow, where I lived at the time, I realized many of the European countries are close to each other, not like the distances I was used to growing up. Canada is close to the United States - and nothing else! Kenya was also vast (not as big as Canada) but it was over a days drive to any border. Europe is different. Everyone is a neighbor to another country - or to many countries.


And Europe has such history. Again, different from Canada. There you talk in 100s of years, but

contrast the old buildings with tiled roofs and the new modern buildings in Tallin
Old with new in Tallinn

in Europe and Asia you see remnants that can be 1000s of years old. By the end of my trip I learned of the history of the area and the different architectural styles - they enthralled and grabbed my imagination. There were old, thick medieval buildings - squat in their physique. But beside them were modern, elegantly decorated buildings. These modern monstrosities spread from the historical medieval walled section like a disease. (see beyond the mediaeval tower - but that is progress.


So, back to the walled city. As you enter, you see how thick the walls are - people lived within the

Shops in the walls of the old walled city that have been modernized and plastered
Shops now exist in the walls of the walled city
Old City walls opened up for cars in old Tallin
Streets going through the old city walls

walls and now there are stores in them. Several roads give access through the walls so now you hardly notice when you are in the old city or in the bigger city that has expanded beyond the ancient walls. The roads within the wall are old, well worn cobblestones which can be hard to walk on for long

Well known passage near the St Catherine's monastery - beautiful arched beams across it
St Catherine's Passage, Tallinn

periods of time. Old walls that have stood for centuries are beautiful in their age and then some are updated with smooth plaster as seen above to the right. One area called St Cahterine's Passage (see to the right) is an ancient path that led to the St Catherine's Monastery (Friary) which is now revamped into a mixed use area - mostly stores and galleries. One wall along this passage displays tombstones that were removed from the monastery when it was converted. There is a central courtyard with Town Hall in the middle and businesses around it - most are restaurants now. Small roads, some are simple alleys, lead out of this courtyard and wind away. This is where the hotels and B&Bs are located, as well as restaurants.


A weekly market spreads colour across the courtyard, selling a variety of touristy things but also artisan products with a local twist: heavy wool sweaters; carved wood products; unique jewelry; art and different memorabilia of Tallinn. Food products, especially homemade breads/jams/local fare, are also available but I would wager that each market day will be slightly different than the previous. The winter market is said to be phenomenal - I just missed it on one of my visits.


Beyond the walls

I am not a morning person but when on holiday, I get up early to experience my surroundings. In

Visiting outskirts of Tallinn shows old wooden houses still standing
Old wooden buildings outside Tallinn

the morning I enjoyed a lovely breakfast and then went out walking to explore the inner city. My very first day I did do the 'Hop on Hop off' bus in order to get an overview - the overall history - with a trip out to a wonderful park and a village that still has the old wooden buildings and the old farms. This is completely different from the modern aspects nearer to Tallinn. I wasn't attracted by too much outside of the city and spent the remainder of my time within the city walls.


Within the Walls: Toompea Hill

One of the stores you pass on the steep climb to Toompea hill, Tallin
Store on climb up hill in Tallinn

I found my way up to the top of Toompea Hill, pretty much the highest point in Estonia and it is in the middle of the walled city. The signs are easy to follow and the map shows how to access it very clearly. it is a steep one, going from one steep 'street' (if you can call them that) to the next alley that takes you to another wider one. (one of the stops is shown to the left) But I assure you the view is worth it. The hike is not for the faint hearted (literally) or anyone with other ills.


At the top there are several buildings to visit; churches, parliament building and Toompea Castle which has a tower, Pick Hermann (or tall Hermann tower). From the top of this you have a bird's

Steep cement stairs up the Pick Hermann tower in Tallin
Climbing the tower on the hill

eye view - a tall tower, on the tallest hill will make it feel that way. The walk up the tower is vertical - no really! It fits the other Medieval structures you see around Tallinn. So hang on to the rope on the side. There are stone steps carved into the tower and only a rope banister to help with your balance. If you make it to the top you are on a floor that allows you to move to the edge and be like a bird!! - that bird's eye view I mentioned.


After going up the tower, (I suggest that first because you need the energy) wander the top area of the hill. It is paved or has stone walkways and courtyards. Find one of the several lookout points and gaze over the old town. You are slightly above the red tiled rooftops. The twisty alleys and small roads are very evident from up there. Look for the wall. You will have glimpses of it and you can really see how thick they are and you get an idea of the size of the old city.

Depending on the day, you can tour the buildings at the top. Or sit on a bench and watch the pigeons swooping down for any scraps. It is peaceful at the top. You might see tour buses unloading their passengers but in general, there is enough room up there to sit and people watch.


Walking the Old Town of Tallinn

Inside the walls are new businesses - some have left the old visible while others revitalize the inside while maintaining the history on the outside. It truly is medieval to modern across the old Tallinn. As you walk around the inner city you can see the smooth cobblestones, worn down by 1000s of years of traffic. Imagine ox carts and horses trudging through the square taking their wares to the businesses of the time. I am sure it was mud originally, before the pebble stones were laid. Behind the huge church, now Town Hall, there is an alley that still has old buildings. In these you have restaurants that boast Medieval re-enactments and menus that represent what might have been on the menu 'in the old days' which is kind of fun to experience. You see men in their vests and puffy sleeves walking the streets (drumming up business for these events) and women in rough linen dresses and a kerchief to cover their hair. It might take you back in time - if just for a moment.


I walked the square and then went through the alley to the next row of 'streets' that circled the square, just to see the layout. These backstreet businesses are still flourishing. I love the signs they have for advertisement and their logos or business names. You can see some below. You can peak through some gates and fences to see even more statues and fun stuff. They ranged from sculptures to stained glass to unique wrought iron. Some that are easily identifiable are the NUKU Puppet theatre and the stained glass ad for the famous Domini Canes Stained glass business. Some I do not know what they are for - the monk with a stein should be a pub but it is not one of the famous 'Monk' bar/restaurants, or the lovers on horseback, or the fun jack rabbit sculpture.


I wish I had some photos of my hotel. I found one from the street that barely shows the doorway (on the right, next to the flag) on the

Street in front of my hotel, Merchant House Hotel
Street of Merchant House Hotel

street that barely shows the doorway. I don't always say the hotel name but this one was super and I believe it has improved since I was there - The Merchant House Hotel. It was built into an old building (a merchant house) which would have had the merchant's business on the main floor and he would have lived above. It is very quaint! There were stairs that led to half levels and then a long hallway with a few steps up and then around a corner to another hallway. At the end of that you take another half-level staircase to a hall that turns the other way and takes you around to the back of the building. I almost got lost getting from my room back to the lobby! The room was spotless with a cozy blankets. It looked out onto rooftops, some tin and some tiled, with an awkward glimpse of an alley that must be behind the building.


A sauna in the basement drew me in after walking the city. And the restaurant, also in the basement but you access it differently, was unique. You could see people's legs going by on the street as you ate. The walls were huge old stone - who knows how old, but much of the rest of hotel had wood - the stairs creaked nicely like any old house should. :) The restaurant took you back in time with candles reflecting off warn stone, some plastered over, to add shadows across the arched ceiling. On some ceilings, the old beams stretched across, still holding up the building. It is a fabulous hotel and great to explore!


The cobbled road that led to my hotel entrance also had restaurants and only a few steps took me to the square almost dead across from Town Hall. Cafes were all along the side, as I mentioned before, and I did eat in them but also tried some of the smaller ones located down the alleys.


The city is on the coastline. I have visited it once from a cruise and enjoyed seeing my favorite parts of the city again. This photo, below, is from the Troompea Hill - where you can see the water.

Beautiful view of Tallinn from the hilltop of Troompea - medieval to modern for sure
Beautiful View of Tallinn



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© 2021 by Bev Baraka/ aka Valerie Bowler
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