A thick layer of snow crunched underfoot and tiny snowflakes swirled above our heads around a skyline filled with Gothic church towers, turrets and stone fortresses. Arriving in Tallinn was like walking into a wintry fairytale. Europe’s best preserved medieval city is a beauty at any time of year, but in the short, cold days of winter, the snow adds an extra touch of magic. In summer you run the gauntlet of stag parties drawn in by cheap beer and budget flights. But in winter the narrow cobbled streets that take you past grand merchants houses, medieval walls and hidden courtyards are almost deserted.
Read more: What to pack for a snowy winter city break
Estonia leads the way in Europe for high-tech industries – it was the first country to allow voting online and has the most start-up companies per person anywhere in the world, including big names like Skype. And its capital Tallinn is a modern coastal city, with trendy neighbourhoods, shopping malls and office blocks. But once you enter the walls of the Old Town you’re transported back in time to the 13th century.
Tallinn’s Old Town started off as a Hanseatic trading post known as Raval, run by a league of German merchants. Its original buildings are so well preserved that the Old Town has been designated a UNESCO World Heritage Site. And it’s particularly amazing to think how well its survived when you look at the turbulent history it’s been through. Tallinn has been invaded by the Danes, Swedes, Teutonic Knights and Russians, it fought the Great Northern War and was bombed in WWII, as well as battling the Nazis, the Soviets, a Great Fire and an outbreak of plague. Despite all that the Old Town is still standing proud.
Fully layered up against the -10 temperatures, we shuffled our way out into the snowy streets to explore. As we walked it took me a while to work out what was missing – cars. The centre of the Old Town is pedestrianised so you can walk wherever you like, and the lack of traffic left the snow a pristine white and the streets peacefully quiet. Snow was piled high along the edges of the pavements, and there were temporary barriers outside buildings whenever the layer of snow balanced on the rooftops or the four-foot-long icicles dangling from the gutters threaten to detach themselves onto passers by below.
If you walk around Tallinn long enough you’re guaranteed to end up in the Old Town Hall Square. This was the heart of medieval Tallinn and started life as a market for the city’s Hanseatic merchants. They built their houses and warehouses around it, still standing and painted in pretty pastel shades of pink, blue and yellow. In summer tables from the surrounding cafés spill out into the square, and in December it’s filled with Christmas market stalls. But in January just the Christmas tree and festive white lights draped across the streets were left. In the centre of the square there’s a stone with a compass rose marked on it – or at least there would have been if it hadn’t been covered in snow. It marks the centre of Tallinn, and if you stand on the spot you can apparently see the tops of Tallinn’s five most famous church spires.
One of the reasons the Old Town has survived so well is the ring of walls and guard towers that stretch around it, protecting it from yet more invasion. The original medieval walls were 2.4km long and there are still 1.9km of them left standing. Only a few of the 66 original defensive towers still remain, but you can climb up to the top of some of the ones that do. With the cold starting to bite we headed up the spiral staircase to the wooden walkway along the top. This was originally where the city guards would wait, looking out for any sign of invaders. But today looking inward you get a beautiful view of the city.
One of the biggest towers is the wonderfully named Kiek in de Kök. It’s a six-storey cannon tower turned museum that protected Tallinn during the Livonian War. It did its job well as there are nine cannonballs still embedded in the walls. The name means ‘Peep into the Kitchen’ because soldiers said they could see into the kitchens of the houses below. As my feet started to go numb in the cold, we retreated indoors into one of the Old Town’s cafés. A lot of the cellars of the merchants’ houses have been turned into cafés and restaurants, with the domed ceilings and candlelight making them a cosy escape from the winter chill. Especially if you warm up with a hõõgwein – Estonian style mulled wine with fruit and nuts.
With the hõõgwein radiating away, we headed away from the Old Town Square and up onto Toompea Hill. Where the lower part of the old town was a bustling merchant town, up above it Toompea Hill was home to the gentry and political elite, heavily fortified to keep the commoners out. The heart of Toompea was the Castle, which has been home to Estonia’s various rulers since 1229. It’s the site of the Estonian Parliament nowadays and has changed a bit since its early days as a wooden fortress. Now there’s an ornate pink baroque building at the front with the rest of an earlier castle tucked away behind it.
Toompea Hill is also home to one of Tallinn’s most distinctive buildings, Alexander Nevsky Cathedral. With its onion-domed roof and gold details it could be straight out of St Petersburg. It was built at the end of the 19th century when Estonia was part of the Russian Empire. It nearly didn’t survive the anti-religious Soviet Era, but was restored when Estonia became independent. But one of Toompea Hill’s biggest attractions isn’t its buildings but the space between them. Tucked down narrow sidestreets are the Kohtuotsa and Patkuli viewing platforms, where a panoramic view of the Old Town opens out below you. Looking out onto Tallinn’s snow-covered roofs, red-tiled turrets and pointy-spired churches was just magical.
We stayed at: Merchants House Hotel, a pair of converted merchants houses (as you’d probably guess!) with lots of original features that’s right on the edge of the Old Town Square. Rooms from £67 a night.
We ate at: The Old Town has a spate of medieval-themed restaurants – all serving wenches and elk soup – so if you’re into that sort of thing head for Olde Hansa or III Draakon. But we went for more contemporary Estonian food. The highlight was Rataskaevu 16 with its modern take on traditional local ingredients but we also liked Porgu, a cellar restaurant with a great beer selection near St Nicholas Church and the ice rink. And if you’re an 80s music fan don’t miss a drink at the Depeche Mode-themed DM Baar.
This article contains affiliate links, where I get a small commission at no extra cost to you – thanks.