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Tallinn’s beautifully preserved medieval Old Town is undoubtedly the city’s heart and soul and a natural gravitation point for tourists to the capital. In fact, with its splendid cobbled streets, red-tiled roofs and elegant spires (not to mention restaurants, bars and shops) it’s no wonder that many visitors to Tallinn never make it outside the Old Town’s ancient walls.
The Old Town can historically be divided into two distinct areas: Toompea Hill and the Lower Old Town, which were separated by a dividing wall since medieval times. The elevated area of Toompea Hill with its castle was occupied by the residences of Tallinn’s rulers and gentry. The Lower Old Town meanwhile developed as an autonomous merchantile centre, flourishing during the 13th-16th centuries, when the city enjoyed membership of the powerful Hanseatic Trading League. Generally speaking these two districts are now collectively referred as the Old Town, however sticklers for precision that we are, you’ll find more information on Toompea Hill on our dedicated page, whilst you can read on to find out more specifically about the treasures and pleasures of the Lower Old Town…

Viru Street is as good a place to enter the Old Town as any, not so much for the McDonalds housed in a bright pink building (still it would be foolhardy to start your tour on an empty stomach), but for the scenic twin turrets – the Viru Gates - that mark your arrival. There are 20 such watchtowers from the city fortifications surviving in Tallinn, from an original 66. All come with a rather fetching red conical roof and add a fairy tale aspect to any trip to the Eesti capital. Make your way down the wide and bustling Viru thoroughfare and you will find all manner of boutique stores, modern malls and street traders. A pleasant taste of commercial Tallinn.
When you hit the end of Viru, veer towards the right and you will find yourself in the very epicentre of the city – Raekoja Plats, or the Town Hall Square. A beautiful space, Raekoja Plats is flanked by the Old Town Hall to the South, the Old Pharmacy to the West and prettily painted townhouses on the remaining two sides. The Old Town Hall is a splendid example of Gothic architecture dating back to the 15th Century, whilst the Pharmacy claims to be the oldest functioning chemists in Europe, and contains a small museum to the medical arts. Once you’ve explored these two stalwarts you can fight for a seat in one of the many restaurants and bars on the square. Sit in the sun or take shelter in the shade of a Saku umbrella.
If you’re prepared to give up your prime spot on the Town Hall Square you’ll still find that the lion’s share of Tallinn’s treasures is yet to be discovered. Head north up Pikk Street and you will find the city’s most famous church, St Olav’s. Legends and stories surround this elegant place of worship which between 1549 and 1625 was the tallest building in the world. Impress your mates by pointing out that the church has been struck by lightning eight times, burnt down three times and its spire was used by the KGB as a radio tower and surveillance point. If you continue down Pikk Street you will find the famous ‘Fat Magaret’ watchtower, the city’s first line of defense against a coastal invasion, and exiting the Old Town you will be heading towards Tallinn’s port.
But don’t jump on the hydrofoil to Helsinki just yet. The Old Town demands your attention for many more hours. In fact one of the best pleasures it can offer is an aimless wander. Throw away your map and guidebook and take pleasure in the simple delights of a stroll in nice environs. After getting lost a few times, and stopping for a cup of coffee, set the compass the south - here you will find another two of the Old Town’s most talked about treasures.
At the bend in Ruuthli street find the most famous of all the Old Town’s bastions – Kiek in De Kok. Scramble up to take a peek into the neighbours’ kitchens. Then scramble back down again and head to the corner of Ruuthli and Niguliste and you will find the gothic Niguliste Kirik. St. Nicholas’ Church was once the place of worship for German knights and merchants; now it’s a museum of religious art and a concert hall for organ recitals at the weekends. (NB. There’s another St. Nicholas’s Church in Tallinn on Vene Street – but this one is a Russian Orthodox church).
Right near Niguliste Kirik you will find the steep cobbled lane named Luhike Jalg ("Short Leg"). The lane is so-called because it offers the shortest route up to Toompea and the castle. Pikk Jalg ("Long Leg") is your other option!
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