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.

[1] 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.

[2] 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.

Until the 19th century, Estonians were essentially serfs under German merchants who dominated the economy. The German big shots were part of the Great Guild, while the German little shots had to make do with the Black Heads Society. This was a union or business fraternity limited to single German men. In Hanseatic towns, when a fire or battle had to be fought, single men were deployed first, because they had no family. Single men were considered unattached to the community and therefore had no opportunity for power in the Hanseatic social structure. When a Black Head Society member married a local woman, he was considered to have a vested interest in the town’s economy and well-being. He could then join the more prestigious Great Guild, and with that status, a promising future economically and politically often opened up.

Today the hall is a concert venue. Its namesake “black head” is the head of St. Mauritius, an early Christian martyr beheaded in Switzerland (A.D. 200). Reliefs decorating the building recall Tallinn’s Hanseatic glory days.

Architecture fans enjoy several fanciful facades along here (including the boldly Art Nouveau #18 and the colorful, eclectic facade across the street).

[3] Great Guild Hall: Pikk, home to the big-shot merchants, feels Germanic because it once was. The Great Guild Hall was the epitome of wealth, with its wide (and therefore highly taxed) front.

Across the street, at #16, the famous Maiasmokk (“Sweet Tooth”) coffee shop, which was the sweetest place in town during Soviet days, remains a fine spot for a cheap coffee-and-pastry break.

[4] Church of the Holy Ghost (Pühavaimu kirik): Sporting a great clock from 1633, the church is worth a visit. The plaque on the wall is in Estonian and Russian. Before 1991, things were designed for “inner tourism” (within the USSR). This church retains its 14th-century design. In back, the old flag of Tallinn—the same as today’s red and white Danish flag—recalls the 13th-century Danish rule. (The name “Tallinn” means “City of the Danes”.) The Danes sold Tallinn to the German Teutonic Knights, who lost it to the Swedes, who lost it to the Russians. Except for two decades in the early 20th century, Tallinn remained Russian until Estonia regained its independence in 1991. The windows are mostly from the 1990s (suggested 15 kr donation, Pühavaimu 2, tel. 644-1487, www.eelk.ee). The church hosts English-language Lutheran services Sundays at 15:00.

• From the church, tiny Saiakang lane (meaning “White Bread”—bread, cakes, and pies have been sold here since medieval times) leads to...

[5] Town Hall Square (Raekoja plats): A marketplace through the centuries, this is the natural springboard for Old Town explorations. The cancan of fine old buildings is a reminder that this was the center of the autonomous lower town, a merchant city of Hanseatic traders. Once this was the scene of criminals chained to pillories for public humiliation and knights showing off in chivalrous tournaments; today it’s full of Scandinavians savoring the cheap beer, children singing on the bandstand, and cruise-ship groups listening to their guides. (While you’ll see few Americans early and late, the old center is inundated with them throughout midday, following the numbered ping-pong paddles carried high by their well-scrubbed, young local guides.)

The 15th-century Town Hall (Raekoda) dominates the square; it’s now a museum, and climbing its tower earns a commanding view. On the opposite side of the square, across from #12 in the corner, the pharmacy (Raeapteek) dates from 1422 and claims—as do many—to be Europe’s oldest. While it’s still a functioning pharmacy, the decor goes back to medieval times and welcomes guests with painted ceiling beams, English descriptions, and long-expired aspirin (Mon–Fri 9:00–19:00, Sat 9:00–17:00, closed Sun). Town Hall Square is ringed by touristy restaurants and inviting cafés. The tourist information office is a block away (behind Town Hall).

• Facing the Town Hall, head right up Dunkri street one block to the...

[6] Wheel Well: The well is named for the “high-tech” wheel, a marvel that made fetching water easier. Most of the Old Town’s buildings are truly old, dating from the 15th- and 16th-century boom-time. Decrepit before the 1991 fall of the USSR, Tallinn is now more affluent and has been quickly revitalized.

• Turn left on Rüütli street and walk two blocks to...

[7] St. Nicholas’ (Niguliste) Church: This 13th-century Gothic church-turned-art-museum served the German merchants and knights that lived in this neighborhood 500 years ago. The Russians bombed it in World War II: In one terrible night, on March 9, 1944, Tallinn was hit, and the area around this church—once a charming district, dense with medieval buildings—was flattened (35 kr, Wed–Sun 10:00–17:00, closed Mon–Tue; organ concerts Sat and Sun at 16:00).

• From the church, turn right and climb the steep, cobbled, Lühike jalg (“Short Leg Lane”). It’s lined with quality Estonian craft shops. At the gate, notice the original oak door, one of two gates through the wall separating the two cities. This passage is still the ritual meeting point of the mayor and prime minister whenever there is an important agreement between town and country. Don’t go through the gate, but continue straight into the view courtyard. Then climb right toward the Russian Cathedral for a good view of the wall.

[8] Danish King’s Garden: Stand in the former garden of the Danish king. The imposing city wall once had 46 towers—the stout, round tower way ahead is nicknamed “Kiek in de Kök.” (While fun to say, it means “Peek in the Kitchen.”) It was situated so that “peek” is exactly what guards could do. (It’s now a small museum with cannons.)

Tallinn is famous among Danes as the birthplace of their flag. According to legend, the Danes were losing a battle here. Suddenly, a white cross fell from heaven and landed in a pool of blood. The Danes were inspired and went on to win. To this day, their flag is a white cross on a red background.

• Walk to the entrance of the onion-domed Russian Cathedral facing the pink palace.

[9] Russian Cathedral and Toompea Castle: The Alexander Nevsky Cathedral was built here in 1900 over the supposed grave of a legendary Estonian hero—Kalevipoeg. While it’s a beautiful building, most Estonians don’t like this church. Built to face the national parliament, it was a crass attempt to flex Russian cultural muscles during a period of Estonian national revival. Step inside for a whiff of Russian Orthodoxy; about a third of Tallinn’s population is ethnic Russian (church free and open daily 8:00–19:00).

Cross the street to the pink palace—an 18th-century addition that Russia built onto the Toompea Castle. Today, it’s the Estonian Parliament building, flying the Estonian flag—the flag of both the first (1918–1940) and second (1991–present) Estonian republics. (Locals say they were always independent...just occupied—first by the Soviets, then by the Nazis, and then again by the USSR.) Notice the Estonian seal: three lions for three great battles in Estonian history, and oak leaves for strength and stubbornness. Ancient pagan Estonians, who believed spirits lived in oak trees, would walk through forests of oak to toughen up. (To this day, Estonian cemeteries are in forests. Keeping some of their pagan sensibilities, they believe the spirits of their departed loved ones live on in the trees.)

• Step left across the parking lot, around the palace, and into the park to see the...

[10] Tall Hermann Tower: This tallest tower of the castle wall is a powerful symbol here. For 50 years, while Estonian flags were hidden in cellars, the Soviet flag flew from Tall Hermann. As the USSR was unraveling, the Estonians proudly and defiantly replaced the red Soviet flag here with their own black, white, and blue flag.

• Backtrack and go uphill, passing the Russian church on your right. Climb Toom-Kooli street to the...

[11] Dome Church (Toomkirik): Estonia is ostensibly Luth¬eran, but few Tallinners go to church. A recent Gallup Poll showed Estonia to be the least religious country in the EU—only 14 percent of the respondents stated that religion is an important part of their daily lives. Most churches double as concert venues or museums. Enter the Dome Church (free, Tue–Sun 9:00–17:00, closed Mon, www.eelk.ee/tallinna.toom). It’s a textbook example of simple Northern European Gothic, built in the 13th century during Danish rule, then rebuilt after a 1684 fire. Once the church of Tallinn’s wealthy, it’s littered with medieval coats of arms, each representing a rich merchant family and carved by local masters—the smaller the coat of arms, the older the family. The floor is paved with tombstones.

• Leaving the church, turn left. Pass the slanted tree and the big, green, former noblemen’s clubhouse on your right (vacated when Germans returned home in the 1930s), and go down cobbled Rahukohtu lane. Local businesses and embassies are moving their offices here and sprucing up the neighborhood. As you pass under the yellow Patkuli Vaateplats arch, notice a ramshackle bit of the 1980s surviving. Just a few years ago, the entire city looked like this. Belly up to the grand viewpoint.

[12] Patkuli Viewpoint: Survey the scene. On the far left, the Neoclassical facade of the executive branch of Estonia’s government enjoys the view. Below you, a bit of the old moat remains. The Group sign marks Tallinn’s tiny train station, and the clutter of stalls behind that is the rustic market. In the distance, ferries shuttle to and from Helsinki (just 50 miles away). Beyond the lower town’s medieval wall and towers stands the green spire of St. Olav’s Church, once 98 feet taller and, locals claim, the world’s tallest tower in 1492. Beyond that is the 985-foot-tall TV tower (much appreciated by Estonians for the heroics involved in keeping the people’s airwaves open during the harrowing days when they won independence from the USSR). During Soviet domination, Finnish TV was responsible for giving Estonians their only look at Western lifestyles. Imagine: In the 1980s, many locals had never seen a banana or pineapple—except on TV. People still talk of the day that Finland broadcast the soft-porn movie Emmanuelle. An historic migration of Estonians flocked from the countryside to Tallinn to get within rabbit-ear’s distance of Helsinki and see all that flesh on TV.

• Go back through the arch, turn immediately left down the narrow lane, turn right, take the first left, and pass through the trees to another viewpoint.

[13] Kohtuotsa Viewpoint: On the far left is the busy cruise port and the skinny white spire of the Church of the Holy Ghost; the spire to its right is the 16th-century Town Hall spire. On the far right is the tower of St. Nicholas’ Church. Visually trace Pikk street, Tallinn’s historic main drag, which winds through the Old Town, leading from Toompea down the hill (below you from right to left), through the gate tower, past the Church of the Holy Ghost (and Town Hall Square), and out to the harbor. The undesirable part of this city of 400,000 is the clutter of Soviet-era apartment blocks in the distant horizon. The nearest skyscraper (white) is Hotel Viru, in Soviet times the biggest hotel in the Baltics, and infamous as a clunky, dingy slumbermill. Locals joke that Hotel Viru was built from a new Soviet wonder material called “micro-concrete” (60 percent concrete, 40 percent microphones). To the left of Hotel Viru is the Rotermann Quarter, an industrial plant revamped into a new commercial zone. Our walk will end there.

• From the viewpoint, descend to the lower town. Go out and left down Kohtu, past the Finnish Embassy (on your left). Back at the Dome Church, the slanted tree points the way, left down Piiskopi (“Bishop’s Street”). At the onion domes, turn left again and follow the old wall down Pikk jalg (“Long Leg Street”) into the lower town. Wander back to Town Hall Square.

[14] Through Viru Gate, to Rotermann Quarter and End of Walk: Cross through the square (left of the Town Hall’s tower) and go downhill (passing the kitschy medieval Olde Hansa Restaurant, with its bonneted waitresses and merry men). Continue straight down Viru street toward Hotel Viru, the blocky white skyscraper in the distance. Viru street is old Tallinn’s busiest and kitschiest shopping street. Just past the strange and modern wood/glass/stone mall, Müürivahe street leads left along the old wall, called the “Sweater Wall.” This is a colorful and tempting gauntlet of women selling handmade knitwear (although anything with images and bright colors is likely machine-made). Beyond the sweaters, Katariina Käik, a lane with top-notch local artisan shops, leads left. Back on Viru street, the golden arches lead to the medieval arches—Viru Gate—that mark the end of old Tallinn. Outside the gates (at Viru 23), an arch leads into the Bastion Gardens, a tangle of antique, quilt, and sweater shops that delight shoppers, and the fine Apollo bookstore (with Internet access and a fine little café upstairs). Opposite Viru 23, above the flower stalls, is a small park on a piece of old bastion known as the Kissing Hill (come up here after dark and you’ll find out why).

Just beyond is Hotel Viru, the Viru Keskus shopping center (with a branch tourist information office, Internet café, supermarket in the basement, and laundry service), and the real world. For a look at today’s Tallinn, browse through the Rotermann Quarter. Sprawling between Hotel Viru and the port, this 19th-century industrial zone is now a much-hyped commercial district with office parks, fancy condos, department stores, and restaurants.

For all the details on Tallin, please see Rick Steves' Scandinavia.

Rick Steves (www.ricksteves.com) writes European travel guidebooks and hosts travel shows on public television and public radio. E-mail him at rick@ricksteves.com, or write to him c/o P.O. Box 2009, Edmonds, WA 98020.

© 2010 Rick Steves