It is hard to miss Tallinn’s multitude of towers. Along with the city’s soaring church spires and distinctive orange roofs, they are a key element of the Estonian capital’s striking skyline. But more than just beautiful architecture, the towers also reveal much about the city’s fascinating history. 

The Old Town Hall, the best-preserved Gothic structure in northern Europe, is an excellent opening example. Originally built in 1322, the building contains a medieval museum, its vaulted ceilings packed full of artistic treasures such as a Gothic bench featuring striking carvings of the story of Tristan and Isolde. Climb its tower to find a wind vane in the shape of an old man wearing a hat and carrying a spear. According to the story, this is Thomas, who as a young boy, successfully shot down a wooden parrot from the top of a high pole during Tallinn’s annual medieval archery contest. No one had been able to complete the task until young Thomas came along and knocked it off in one go. He was subsequently made an apprentice guard and became an expert soldier; the city made the metal statue after his death so he could continue to protect the city from his vantage point.

Another impressive spire belongs to nearby St Olav’s church. The tallest structure in the Old Town at 123.7m, the 12th-century church has been hit by lightning a dozen times and burned down and rebuilt three times. However, it still stands proud today, and its tower – accessed via a narrow and vertiginous flight of circular stairs that lead out onto a viewing platform – provides some of the most breath-taking views of Tallinn. According to legend, when the tower was first being built the tower’s construction kept mysteriously failing. But then a stranger appeared, saying he would get the job done if the townsfolk either paid him lavishly in gold or could guess his name. Spies were employed to find out, and one day, just as the stranger was putting the finishing touches on the tower, men from the town crowded around the church and began to shout: “Be careful Olav, the cross is not straight” – whereupon the man, shocked at hearing his name, fell from the tower, hit the ground and died . As a wall carving in the adjacent Chapel of Our Lady reveals, a snake and a toad then crawled out of Olav’s mouth and all three were subsequently turned to stone.

Tallinn’s 4m-thick city wall carries equally enigmatic tales. Constructed in the late-14th Century to fend off invaders, there were once 45 towers helping to form the city wall. By the 16th Century, Tallinn was one of the most fortified cities in world as the walls were raised to 16m high to better defend against cannon fire from potential invaders.

While many of the towers have been destroyed, an impressive 26 remain – helping to solidify the city’s status as a Unesco World Heritage Site. Along with Viru Gate, they form a striking entrance to the city’s chocolate-box Old Town. One of the most famous towers is the artillery structure Kiek in de Kok. Its sore-sounding name, derived from German, actually means Peep in the Kitchen, a reference to the fact that the tower’s guards could look into the kitchens of nearby houses. About 38m high, its thick walls still carry the scars of medieval warfare and close inspection will reveal 16th-century cannonballs embedded in the structure. Though Kiek in de Kok fell out of use in the 18th Century, the tower has since been restored; used for a short time for training rooms for Estonian athletes, it now features exhibitions of Tallinn’s medieval life and military history, complete with finds from the Late Iron Age, replicas of torture equipment and exhibits about the plague.

The cafe on the tower’s top floor gives great views over Toompea, Tallinn’s upper town. Look across to St Mary’s Cathedral – the oldest church in Tallinn, known to locals simply as the Dome Church because of its curved towers – and the distinctive Alexander Nevesky Russian Orthodox church which dominates Toompea. The latter, built to “Russify” Estonia in the late 1800s, was a symbol of oppression for many years, but plans to destroy it in the 1920s were shelved due to lack of funds. Today it is one of the city’s main tourist sites.

Also in view is Neitsitorn (the Virgin’s Tower), another part of the city wall that has medieval battle scars; it got its name from being used as a prison for prostitutes. Legend has it that the prison was so haunted, terrified prisoners regularly asked to be relocated. Reports of ghosts continue to the present day; the latest relating to a wine-drinking monk who supposedly occupies the cellar.

From the bottom of the Virgin’s Tower, enter the tree lined Danish King’s Garden, from where another tower – with a ghost story attached – can be seen. The quirky, square-shaped Short Leg Gate Tower at the top of Lühike Jalg (or Little Leg street) is supposed to be one of most haunted; regular sightings include a monk (reputedly a former executioner with a guilty conscience) and a floating woman bedecked in medieval dress.

At the other end of the city near the harbour is yet another famous tower, Fat Margaret (Paks Margareeta). With its 5m walls, even thicker than Kiek in der Koek, its name allegedly comes from German sailors who saw it from a distance and named it Dicke Margaret, though other stories suggest it comes from the large cannons used or even a portly chef called Margaret who once cooked for the guards. Since 1981 the tower has contained the Estonian Maritime Museum which details the nation's seafaring past; the roof of the tower, which has 360-degree views of the harbour and city, can be accessed as part of a museum ticket or separately

While the majority of the city’s story-infused high points are in the Old Town, there are a couple worth investigating outside. The huge Hotel Viru, built in 1972 on the eastern fringes of the Old Town, was used in Soviet times as the main hotel for visiting dignitaries or media. They could be spied on during their stay from an “invisible” 23rd floor that didn’t show up in the lift (the display only showed 22 levels) and was only accessible via a plain and permanently locked door that was disguised as a cupboard. Today the former KGB headquarters is a museum containing fascinating stories about the clandestine activities that took place there.

The city’s 314m-high TV tower, Tallinna teletorn, also cannot be overlooked. Built in 1980, it reopened in 2012 after extensive renovations. Though most people visit for the excellent vistas and the gourmet restaurant, the tower was the location of choice for the radio-jamming rebel troops who foiled the Russians when they tried to reoccupy Tallinn in August 1991.