Although first populated more than 10,000 years ago, Tallinn Estonia was initially settled by local craftsmen and merchants in the 11^th century and was officially conquered by and designated as a city by Denmark in the 12^th century. An influx of German merchants helped to establish Tallinn as a major trading power and leading and prosperous Hanseatic League city in the 13^th century.

But Tallinn, along with the rest of Estonia, has never maintained an identity of its own for long. It was sold to Germany in 1346, divided into three parts (among Germany, Denmark and Poland), captured and developed (as with a public education system and its first university) by Sweden and lost to Russia in the 18^th-century Great Northern War. After that, its merchant economy stumbled as Peter the Great effectively established the country and city as a summer resort for wealthy Russians—including himself and his Estonian wife, Catherine. It remained under Russian control until 1918, when the country declared and, after a brief war (with support from a number of allies) won its independence from a Russia that was embroiled in its own revolution.

This independence lasted only until 1940 when Germany and Russia entered into an agreement that gave Russia permission to occupy and establish its own military bases in the country. That lasted only until 1941 when Germany seized and maintained control of the country through 1944, when the Russians effectively conscripted the Estonia into the Soviet Union and maintained control until 1991. This has resulted in the longest period of independence in the country’s long history—25 years and counting. Over this period, the county has dramatically built its economy, and maintained a reasonable relationship with Russia while simultaneously building ties to Scandinavia and Western Europe (as through membership in both the EEU and NATO) and reestablishing itself as something of a crossroads between western and eastern Europe.

The Medieval City

The city is effectively divided into two very different parts—a beautifully restored medieval-era Old Town and a modern New Town. We spent most of our time in Old Town. This ancient area consists of two primary sections that used to be separated by gates, but were combined into a single city in 1878:

• Upper Downtown, a 13^th century hilltop area created around the city’s original fortress had been home to the city’s nobility and wealthy merchants; and
• Lower Old Town, which radiates out from the 14^th-century Town Hall Square, and used to be home to regular citizens, workshops and shops.

Although about 12 percent of the city was destroyed by Soviet bombs in an attempt to dislodge the Germans, both parts of the historic old town have been almost totally rebuilt.

Upper Old Town and Toompea Hill

This area grew around the original 13^th-century hilltop fortress. It includes some of the remaining city walls, two tall and important, 14^th-century towers (Maiden and Pikk Hermann) and a roughly 300 meter stretch of the underground bastions (Kiek-in-de-Kok Bastion) that connected the towers. This most historic section of the city also contains several important structures.

These include:

• Toompea Castle, a pretty, pink, Baroque-style building that has traditionally served as the headquarters for whichever foreign power happened to control the country at a particular time, It now serves as the independent country’s Parliament building.

• Alexander Nevsky Cathedral, a grand, neo-Byzantine Russian Orthodox cathedral that was built by the Russians between 1894 and 1900. The huge, ornate, domed cathedral dominates the square and with its location atop the hill, sent (whether intentionally or not) a message to the people of the city—a message of Russia’s dominant power.

• Cathedral of Mary the Virgin, a Gothic-style church that was built in the same location as a 1240 Danish wooden church of the same name, making it the oldest church in the country. Although the exterior is quite plain, the interior is highly decorated with a Baroque pulpit and several coats of arms.

• Knight’s House, an 1848 neo-Renaissance-style meeting place for the city’s influential knighthood.

• Stenbock House, which contains the office of the Prime Minister and the Chancery.

Lower Downtown and Town Hall Square

The Town Hall Square area was founded at and grew around the 1404 fortress-like Town Hall building and the large square that spreads out around it. The square, which is generally acknowledged to be the first in Europe to display annual Christmas trees (a practice begun in the early 15^th century), hosts marketplaces (including the city’s popular Christmas Market), civic functions and celebrations.

The primary landmarks in this section of the city are:

• Town Hall, a large, intimidating structure and city symbol that was first mentioned in preserved documents in 1248 and expanded to its current size in 1404. The structure is topped by a tall Renaissance spire and, as a break in the solemnity, is surrounded by fun, dragonhead-shaped waterspouts. The history of the building, its interior and its historical exhibits are discussed in our Tallinn Museum post.

• Viru Gate, South Gate, the City Walls and Fat Margaret’s Tower. The two towers of 14^th century Viru Gate (one of the primary entries into the Old City), about half the original 1.85 kilometer city wall and many of the 40 original towers (including Fat Margaret’s Tower, which contain the thickest part of the wall at 13-feet) all remain intact. The South Gate, meanwhile, is a visible only as a glassed-in excavation. All, however, are impressive and the walls are accessible to anyone who wants to walk them.

• Holy Spirit Church, a lovely 13^th-century Gothic structure with original stone carvings, the oldest public clock in the city and a number of religious artifacts, including a 15^th-century alter triptych.

• Great Guild Hall, a large, Gothic-style members club and hall that was built by wealthy Hanseatic League merchants in 1417 and now contains the Estonian History Museum (see our post on Tallinn Museums).

• Niguliste Church, commissioned in the mid-13^th century by German Hanseatic merchants, this grand church, originally named St. Nicholas, was built as part of the city’s fortifications. It is, as discussed in our Tallinn Museum post, now a museum that contains a number of the many of the city’s most important religious masterpieces.

Additional historic Lower Old Town sites include:

• St Catherine’s Passage and Salakang Alley, two small medieval alleys, each with their own charms. St. Catherine’s, next to the old church, is entered through an arch, surrounded by uneven, ancient stone walls and lined, on one side, by 14^th-century gravestones on one hand, and cafes and artisan shops on the other. Salakang, meanwhile, is a narrow alley that opens onto a charmingly narrow building that sits alone, in the middle of a small square.

• House of Blackheads, a meeting place (built in 1399, with the front renovated in 1597) for a group of well-to-do, but unmarried (and therefore, ineligible for membership in the Guild) merchants who had the duty of defending the city in case of attacks. The front of structure displays the brotherhood’s carved coat of arms and busts of the then king and queen.

• St. Olav’s Church, with its 407-foot spire, remains (by law) the tallest building in the county. This is despite the fact that it was struck by lightning at least eight times, and was twice burned down and replaced. (Note, the tallest building, does not mean the tallest structure. This honor goes to the 1.030-foot TV tower built by the Soviets in 1980.)

• Town Hall Pharmacy, whose documented history at this location goes to 1422, but is thought to be at least 100 years older. While still operating as a pharmacy, it contains a number of historical displays and descriptions of earlier pharmaceutical devices and practices.

The large, open, Freedom Park is built on a stretch between Upper and Lower Old Town Areas. Towered over by a 24-meter cracked-glass cross, it hosts large public presentations (including one by the Dali Lama) and concerts.

Although the city certainly has more than its share of large, historic and particularly notable buildings, the real joy is just in exploring the streets, where you come across all types of beautiful, old structures, diverse styles, lovely decorative elements and scenic combinations of different color buildings. A handful, originally built as warehouses, still support the winches and the upper-story doors that were used to lift loads from the street into the top floors of the building.