Walking Tour: Tallinn’s Old Town

  • Start Freedom Square
  • End Viru Gate
  • Length 4km; three hours

We've designed this walk as an introduction to Tallinn's meandering medieval streets. Starting at Freedom Square (Vabaduse väljak), take the stairs up into Toompea, noting the stout walls and famous Kiek in de Kök tower on your right, and the Independence monument on your left. Continue to Linda Hill, from where you can see the remaining medieval elements of Toompea Castle; backtrack and turn left onto Castle Square (Lossi plats) for a view of its baroque facade. Directly across the square is onion-domed Alexander Nevsky Orthodox Cathedral.

Take Toom-Kooli to Toompea’s other cathedral, St Mary's and cut across Church Sq (Kiriku plats) onto Rahukohtu, where a lane leads to the Patkul lookout (Patkuli vaateplats), offering terrific views across the lower town to the sea. Continue winding around the lanes to the Court Square lookout (Kohtuotsa vaateplats).

Take Kohtu and Piiskopi behind both cathedrals and head through the opening in the wall to the Danish King’s Garden, where artists set up their easels in summer to capture the ageless vista over Tallinn's rooftops. Exit to the left and then take the steps up through the Short Leg Gate Tower, which is thought to be the most haunted building in Tallinn. Ghostly apparitions have been reported inside this tower, including a crucified monk and a black dog with burning eyes. Turn right and take the long sloping path known as Long Leg (Pikk jalg) through the red-roofed Long Leg Gate Tower (1380) and into the lower town.

Turn left along Nunne and then veer right onto Väike-Kloostri where you’ll come to the best-preserved section of the Lower Town Wall, linking nine of the 26 remaining towers (there were once 45). Pass through the gate and turn right for a better view. Wander through the park to the next small gap in the walls and re-enter onto Aida. At the end of that street, turn left onto Lai, which is lined with 15th-century German merchants' houses; many extend to three or four floors, with the lower two used as living and reception quarters and the upper ones for storage.

At the very end of Lai, follow the small path to the right alongside the wall to the Great Coast Gate, the most impressive of the remaining medieval gates. Note the crest on the outside wall and the crucifix in a niche on the town side.

As you head up Pikk, spare a thought for those who suffered at number 59, the former KGB headquarters. The building’s basement windows were bricked up to prevent the sounds being heard by those passing by on the street. A small memorial on the wall translates as: ‘This building housed the headquarters of the organ of repression of the Soviet occupational power. Here began the road to suffering for thousands of Estonians.’ Locals joked, with typically black humour, that the building had the best views in Estonia – from here you could see all the way to Siberia.

Further along Pikk are buildings belonging to the town’s guilds, associations of traders and artisans, nearly all German-dominated. First up, at number 26, is the Brotherhood of the Blackheads (Mustpeade maja). The Blackheads were unmarried young men who took their name not from poor dermatology but from their patron, St Maurice (Mauritius), a legendary African-born Roman soldier whose likeness is found on the building facade (dating from 1597), above an ornate, colourful door. Its neighbour, St Olaf’s Guildhall (Olevi gildi hoone), was the headquarters for what was probably the first guild in Tallinn, dating from the 13th century. Its membership comprised more humble non-German artisans and traders.

Next up is the 1860-built St Canute’s Guild Hall, topped with zinc statues of Martin Luther and the guild's patron saint. A little further down the road is the 1410 headquarters of the Great Guild, to which the most eminent merchants belonged, and which is now an intriguing museum.

Cross the small square to the left, past the photogenic Holy Spirit Church and take narrow Saiakang ('White Bread Passage' – named after a historic bakery) to Town Hall Square. Continue left to Vene (the Estonian word for Russian, named for the Russian merchants who once resided and traded here) and cut through the arch into Katariina Käik. At the far end, turn right and left again onto Viru, one of Old Town’s busiest streets. Finish at the Viru Gate, which connects Old Town with the commercial centre of the modern city.