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).
 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.
 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...
 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...