Tallinn Old Town

Soviet rule was a sort of blessing in disguise for Tallinn’s old city. Yes, there was the small matter of the Soviet air force bombing and strafing Tallinn on one day in 1944—an attack which flattened 11 percent of the old quarter (See remnants of the attack on Harju street). And during Soviet rule there was gross neglect of historic structures. On the other hand, economic stagnation then meant development was kept to a minimum. So, unlike Helsinki—scarred by decades of development projects—Tallinn’s old city has remained much the same. In ways, it’s changed more in the past five years than it did in the previous 100. It now has many things city merchants in days of yore certainly did not: like a McDonald’s. Other changes, like cheesy neon signs and a few new modern buildings, must have some Tallinn founding fathers spinning in their graves. But, all in all, the old city has kept its charm. Some better-known sights:

The Upper Old City—or Toompea Hill (I-1)—is the oldest part of Tallinn, inhabited since pre-history. Throughout the Middle Ages and into the 19th century it was the main residence of the aristocracy and clergy, who were immune from the dictates of Tallinn city law. In addition to having Tallinn’s oldest buildings, it has good viewing platforms; the best one is at the end of Kohtu street (I-2). Toompea Castle (I-1) is one of Estonia’s most treasured landmarks, built by Danes and Germans after they defeated the Estonians in the early 1200s. The nation’s oldest church—Toomkirik (Dome Church)—is also on Toompea (I-1); built in 1223, it’s a burial site of German and Swedish noblemen. Aleksandr Nevsky Cathedral (I-1) is an Orthodox church built in 1900; some say the Czar purposely built the church on the grave of epic Estonian hero Kalev and regard the cathedral as a symbol of efforts to russify Estonia.
The defensive wall ringing the old city is the town’s most striking feature. While Riga and Vilnius’s walls were destroyed, 80 percent of the original 2.35-kilometer-long wall around Tallinn in the 1500s is still intact today; out of 27 towers, 18 have survived assorted sieges and bombardments. The wall served the city well in the days of the crossbow, but became obsolete as firepower increased in the 1600s. One watch tower is Neitsitorn (Virgin’s Tower); in medieval times it was a prison for prostitutes (I-1); it’s now a café.
Town Hall Square (I-2) is the hub of the Lower Old City. It was a gathering place for traders even in pre-history and has been a city focal point for 800 years. It was also the place for public executions; on one day in 1806, 72 people were executed following a peasant revolt. The Town Hall, built in the 1200s, was the seat of the Town Council, a sovereign power within the city walls. Except for the spire (which you can climb), the building’s changed little in 500 years. The weather vane on the spire has become a Tallinn mascot; this figure of a 16th century guard is named Old Toomas in honor of an actual guard much loved by children in the city. In the northeast corner of the square is one of the longest continuously-functioning drug stores in the world, the Town Council Pharmacy, or Raeapteek; it first opened its doors in 1422, 70 years before Columbus discovered America. It once sold powder made—allegedly—from unicorn horns and a range of herbs. On the square, look for the L-shaped stones where a priest was beheaded in 1694. He axed a waitress to death after she served him an omelette he didn’t like. Said one account: “She served him an omelette as hard as a shoe.” The old city jail is also on the square, at Raekoja plats 4/6; it’s now a gallery.
To the west is the Oleviste Church (St. Olaf’s) (H-3), built in the 1200s and rebuilt in the 1400s. An architect named Olaf fell to his death from atop the tower; legend has it that when his body hit the ground, a snake and toad crawled out of his mouth. Until 1991, the KGB used Oleviste’s spire as a radio tower. At the end of the street is Fat Margaret (Paks Margareeta) (G-3)—the city’s quirkiest-looking guard tower. Built in the 1500s, it derived its name from a stocky cannon in the tower—but could have just as well got the name from the beefy look of the tower itself; from 1830-1917 it was a prison. At Pikk 71 are the Three Sisters—three almost identical medieval houses. At Pikk 61 is the ex-KGB headquarters; now the Interior Ministry, it had cells where prisoners were caged prior to deportation. One Soviet-era joke was that this was the world’s tallest building because, from the cellar, you could see Siberia.
Another watchtower is the 15th century Kiek in de Kök, or Peep into the Kitchen, on Harjumägi, off Vabaduse Square (J-1). Watchmen were able to see into kitchens from atop the tower—hence its name. On the front of the tower are Russian cannon balls that supposedly became stuck when the Swedish-ruled city was being bombarded during the Livonian War, 1558-1583. Nearby, at Rüütli 16/18 (J-2), is the house where Tallinn’s town executioner lived. It’s now a fish restaurant, Mõõkkala. In the Middle Ages, the executioner was responsible for meting out punishments, from beheadings to various tortures. He was shunned by residents and coming into contact with him was thought to bring bad luck. Neither he nor his wife were allowed to attend church, and his children couldn’t go to school. An inscription on the executioner’s sword read: “God’s mercy and faith are renewed every morning. Raising this sword, I help the sinner find eternal rest.”

Parliament: The parliament, or Riigikogu, is in Toompea Castle (I-1); the main hall is in a lovely Expressionist style. Tours Mon., Wed., Thu. and Fri., 10:00 -16:00. Call in advance, tel. 631-6357.

Linda Monument: A pre-war sculpture that later became a memorial to victims of Stalinist terror. Located off Falgi (J-1), it depicts Estonian epic figure Linda mourning her husband Kalev’s death. In Soviet times, some brought flowers here in memory of those deported or killed—a gesture which could land you in prison. There’s now a plaque by the statue reading, “To remember the ones taken away.”

Russian Embassy: Once a hot-bed of KGB activity, Russia’s embassy—at Pikk 19 (H-2)—is now a more traditional foreign representation. Its Pikk balcony is infamous: in 1940, Stalin’s henchman Andrei Zhdanov stood here overseeing a staged demonstration by Communists calling for Estonia to be “accepted” into the USSR; within days, its forcible annexation was complete.

Rataskaevu street: (I-2 ) A 700-year-old street, one of Tallinn’s oldest. There’s a well here where a goblin was thought to live. Tallinners once threw cats down the well to appease the demon. According to legend, the devil celebrated his wedding in Rataskaevu 18; the clinking of goblets can still supposedly be heard at midnight.

Dance of Death: A painting by Berndt Notke (1440-1509) in the St. Nicholas Church (I-2)—a museum of medieval art. The painting testifies to a death obsession in Medieval times.

Dominican Monastery: A 13th century monastery, Vene 16 (I-3). During the Reformation, it was plundered and made an armory. In 1531, a vengeful monk burned it down. See the nearby Katariina Passage.

Pikk Jalg Gate Tower: (I-2) A 14th century tower, once the only entrance to Toompea—the domain of nobility.

Pühavaimu Church: (I-2) The Holy Ghost Church is one of Tallinn’s oldest—first mentioned in 1316; 500-year-old street clock.

The Estonia Monument: A memorial to ferry Estonia; 850 people died when the ship went down en route to Stockholm in 1994. On the edge of the old city (G-3).