Metravel city quest
City Tallinn: free walking route “quest: Old Thomas and two towns” along the sights. 13 points. Approximately 3 h. Quests and legends - straight from your
The city’s very name preserves its divided nature. “Tallinn” is most often interpreted as “Taani-linn” — “Danish town”: in 1219 the Danes landed on this shore, defeated the Estonians and built a fortress on the high limestone hill of Toompea. Seven centuries later the city was still called Reval — “Tallinn” only became the official name in 1918, when Estonia first became independent.
But this quest is not about the kings and bishops who lived above, on Toompea. It is about a boy named Toomas. According to legend, he was an ordinary village lad who once came to the spring crossbowmen’s contest — shooting at a wooden parrot on a pole, a pastime of wealthy townspeople. Toomas shot better than anyone. But he received no prize: a boy of humble birth had no business outdoing distinguished burghers. Instead, he was offered a position as a city guard — for life. Toomas served the city faithfully, treating children in the square to sweets throughout his life, and when he died the townspeople made him an eternal lookout — a figure of an old warrior with a weather vane on the Town Hall spire. Since 1530 Old Thomas, Vana Toomas, has looked down over Tallinn and, as people say, “sees, hears and knows everything”.
We will walk through the city through his eyes: starting high on Toompea, where those who never invited the boy to their feast lived, descending through the old gate into the Lower Town to Town Hall Square, where Toomas has been on watch for a fifth century, and following Pikk Street all the way to the sea, where the city once welcomed and saw off Hanseatic ships.
What to do: 1) Read the story and task at each point. 2) Find the place on the map and walk up to it. 3) Look around and answer the question.
The Old Town is a UNESCO World Heritage Site — one of Europe’s best-preserved medieval centres. This is a walking route of about two and a half kilometres, entirely on cobbled streets and stairs. We begin at the very top, beside Pikk Hermann tower.
The route points in order — what these places are and why they are interesting. Tasks and answers stay inside the quest.
Pikk Hermann — “Tall Hermann” — is the oldest of Toompea Castle’s four corner towers: its first level was built in 1360–1370, and in the 16th century it was raised to its present 45.6 metres.
Descend from the area beside Pikk Hermann to Castle Square (Lossi plats) — and you will see a five-domed Orthodox cathedral with gilded cupolas, as though brought here straight from Russia.
Walk around the cathedral along the fortress wall — and almost immediately you will find yourself in the Danish King’s Garden, squeezed between the cathedral and the city wall.
Climb back uphill to Toom-Kooli — there stands the oldest church in mainland Estonia, the Dome Church. Founded as early as 1233, soon after the Danish conquest, it is the only building on Toompea to have survived the great fire of the 17th century.
From the Dome Church, follow Kohtu — a short street that ends right at the edge of Toompea’s cliff. Here, at the Kohtuotsa viewing platform, the entire Lower Town lies spread out below you: tiled roofs, spires and a glimpse of the harbour in the distance.
From the viewpoint, descend towards Lühike jalg gate — the “Short Leg”. This is one of two medieval stair-streets that for centuries were the only connection between the upper and lower towns — the other, Pikk jalg, the “Long Leg”, took a gentle slope for carts and horsemen, while this shorter, steeper one was only for pedestrians.
At the foot of the stairs, turn onto the short Niguliste tänav — there stands Niguliste Church, dedicated to St Nicholas the Wonderworker, patron of sailors and merchants: Westphalian traders founded it back in the 13th century.
Here is the heart of the Lower Town — Town Hall Square, Tallinn’s centre of trade and justice for almost eight centuries. The Gothic Town Hall before you was completed in stages from 1402 and remains the only medieval town hall in Northern Europe preserved in its original form.
From the square, turn onto Vene Street — “Russian Street”, named after the quarter where Orthodox merchants lived for centuries — and after a few steps slip into St Catherine’s Passage. Old tomb slabs from the 14th–17th centuries are set into the passage wall — surviving fragments of the monastery’s cemetery.
This stop is optional, but a pity to miss. Return to the square and turn onto Pikk Street — we will now follow it all the way to the sea.
Continue north along Pikk — Hanseatic merchants walked this street for centuries, and their houses still stand on both sides. On the way you will pass three narrow Gothic façades that townspeople have long called the Three Sisters: a merchant built the middle house in 1362, with its neighbours added later, each a little narrower than the previous one.
Ahead is the very spire you were looking for from the Kohtuotsa viewpoint. Oleviste Church, dedicated to the Norwegian saint-king Olaf, is first mentioned in 1267; according to tradition, it was built even earlier by Scandinavian merchants who honoured Olaf as the patron of sailors.
It was built in 1511–1530 as part of the Great Sea Gate: from here the city welcomed ships coming into the harbour and sought to impress foreigners with its might. The tower’s name could not suit it better: its diameter is 25 metres and the walls of the lower level are about five metres thick.
This route is part of Metravel city quests. Below are the other quests in this city and cities with quests nearby.