The quiet streets north of Raekoja Plats (Town Hall Square) contain most of Vanalinn’s finest museums. These institutions are primarily located on Pikk tanav (Long Street) and Vene tanav (Russian Street), which run north-south. The area’s greatest charm, however, lies in the lanes connecting these thoroughfares and popping into whatever building (there are many artists studios) or café seems appealing.
As its name suggests, Pikk tanav is Vanalinn’s longest street, running from the Great Coast Gate up Toompea (where its name changes to Pikk jalg meaning "Long Leg"). As you enter the Great Coast Gate from Raanamae tee, you’ll notice a white cross and a large granite monument inscribed with the names of the 852 people who died when the MS Estonia car ferry between Tallinn and Stockholm sank in the early hours of September 28, 1994, under mysterious circumstances that a contemporary official report ascribed to a leaky bow door. Just 137 of the people onboard survived the disaster, the worst in peacetime European history, and the occasion of its tenth anniversary led to renewed calls for the a reexamination of the evidence.
The Great Coast Gate is the northernmost and best-preserved of Vanalinn’s medieval gates, as well as the closest to its harbor. During the 16th century, it was further fortified by the construction of the so-called "Fat Margaret", a bastion with four-meter-thick walls that today houses Estonia’s Maritime Museum. The major guild halls of the medieval city line Pikk. The Great Guild, which comprised the city’s most prosperous merchants, had was located at number 17, today home to the pre-1850 collections of the State History Museum. The German artisans made do with St. Canutus Guildhall at number 20 (although note that the present structure dates only to the 1860s), while their humbler non-Teutonic counterparts made do with St. Olaus Guildhall at number 26. The Brotherhood of the Blackheads (unmarried merchants) is at number 24 and particularly notable for its fine carved door.
Visible from Pikk but actually located on nearby Lai tanav (Wide Street) is St. Olaf Church, originally built in 1267, whose landmark 123.7m tower once reached to 159m, making it the tallest building in the world. Local legend holds that dark powers were involved in its construction, and as with much in Tallinn, the tourist industry is only too eager to give it credence. (Please see my entry "St. Olaf's Church" for details.) The inside of the church itself is fairly uninteresting; however, the view from its tower is the best vantage point anywhere in the city (including Toompea). Consequently, it’s hardly surprising that the KGB had a surveillance point here! After climbing down, reward yourself with a pastry and coffee at Maiasmokk (Sweet Tooth), Tallinn’s oldest café, dating to 1865. It’s also the city’s finest, so you may have difficulty finding a seat in the beautiful Art Nouveau tea-room.
The excellent City Museum at Vene 17 provides an extensive collection, not just of Tallinn but also of Estonia generally. It covers the entire period from the city’s foundation to restoration of independence under a single roof. The building it occupies was once a medieval merchant’s home, which the exhibits make good use of, but its collection of artifacts range from the prehistoric to television monitors showing footage from the "Singing Revolution" and the country’s subsequent Eurovision Song Contest victory in 2001.