This walk explores the “two towns” of Tallinn. The city once consisted of two feuding medieval towns separated by a wall. The upper town—on the hill, called Toompea—was the seat of government ruling Estonia. The lower town was an autonomous Hanseatic trading center filled with German, Danish, and Swedish merchants who hired Estonians to do their menial labor.
Two steep, narrow streets—the “Long Leg” and the “Short Leg”—connect Toompea and the lower town. This walk winds through both towns, going up the short leg and down the long leg. If you’re coming from the ferry terminal, you’ll enter the town at #1 (see map). If you’re coming from Town Hall Square, walk out to the Fat Margaret Tower.
 To Fat Margaret Tower and Start of Walk: From the ferry terminal, hike toward the tall tapering spire, go through a small park, and enter the Old Town through the archway by the squat Fat Margaret Tower. Just outside the tower on a bluff overlooking the harbor is a broken black arch, a memorial to 852 people who perished in 1994 when the Estonia passenger ferry sank during its Tallinn-Stockholm run. The details remain murky, and conspiracy theorists still think Sweden sank it. (The boat went down very quickly; Sweden has never allowed any divers to explore the remains, and now there’s talk of entombing it in concrete, leading some to believe the incident involved some kind of nuclear material-related mischief.)
Fat Margaret Tower guarded the entry gate of the town (in medieval times, the sea came much closer to this point than it does today). The relief above the gate dates from the 16th century, during the Hanseatic times, when Sweden took Estonia from Germany. (The paltry Estonian Maritime Museum in the tower costs 50 kr and is open Wed–Sun 10:00–18:00.)
Just inside the gate, you’ll feel the economic power of those early German trading days. The merchant’s home nicknamed the “Three Sisters” (on your right with your back to the sea) is a textbook example of a merchant home/warehouse/office from the 15th-¬century Hanseatic Golden Age. The charmingly carved door near the corner evokes the wealth of Tallinn’s merchant class.
• Head up Pikk (which means “long”) street.
 Pikk Street: This street, the medieval merchants’ main drag leading from the harbor up into town, is lined with interesting buildings—many were warehouses complete with cranes on the gables. You’ll pass St. Olav’s Church (Oleviste Kirik, a Baptist church today), notable for what was once the tallest spire in Scandinavia. Its plain whitewashed interior is skippable, though climbing 234 stairs up the tower rewards you with a great view (church entry free, daily 10:00–18:00; tower-30 kr, open April–Oct only; www.oleviste.ee).
While tourists see only a peaceful scene today, locals strolling this street are reminded of dark times under Moscow’s rule. The KGB used the tower at St. Olav’s Church to block Finnish TV signals. And the ministry of police (nearby at Pikk 59) was, before 1991, the sinister local headquarters of the KGB. “Creative interrogation methods” were used here. Locals well knew that “from here started the road of suffering,” as Tallinn’s troublemakers were sent to Siberian gulags. The ministry building was called “the tallest building in town” (because “when you’re in the basement, you can already see Siberia”). Notice the bricked-up windows at foot level.
The Navitrolla Gallerii (at #36) is much happier, filled with art by a well-known Estonian artist. His whimsical, animal-themed prints are vaguely reminiscent of Where the Wild Things Are (Mon–Fri 10:00–18:00, Sat–Sun 10:00–16:00, next to Hell Hunt Pub, tel. 631-3716, www.navitrolla.ee).
Farther up Pikk, the fine Hall of the Black Heads Society (at #26) dates from 1440. For 500 years, until Hitler invited Estonian Germans “back to their historical fatherland” in the 1930s, this was a German merchants’ club.