Gamla Stan, The Old Town, consists primarily of the island Stadsholmen. The town dates back to the 13th century, and consists of medieval alleyways, cobbled streets, and archaic architecture. North German architecture has had a strong influence in the Old Town's construction. Gamla Stan is one of the best preserved old towns in Northern Europe.

The center of Gamla Stan is Stortorget, the scenic large square, which is surrounded by old merchants' houses including the Stockholm Stock Exchange Building. The square was the site of the Stockholm Bloodbath, where Swedish noblemen were massacred by the Danish King Christian II in November, 1520. The following revolt and civil war led to the dissolution of the Kalmar Union and the subsequent election of King Gustav I.

As well as being home to the Stockholm Cathedral, the Nobel Museum, and the Riddarholm church, Gamla stan also boasts Kungliga slottet, Sweden's baroque Royal Palace, built in the 18th century after the previous palace Tre Kronor burned down. The House of Nobility (Riddarhuset) is on the north-western corner of Gamla stan. The restaurant Den gyldene freden is located on Österlånggatan. It has been in business since 1722 and according to the Guinness Book of Records is the oldest existing restaurant with an unaltered interior. A statue of St. George and the Dragon (sculpted by Bernt Notke) can be found in the Stockholm Cathedral, while Riddarholmskyrkan is the royal burial church. Bollhustäppan, a small courtyard at Slottsbacken behind Finska kyrkan, just south of the main approach to the Royal Palace, is home to one of the smallest statues in Sweden, a little boy in wrought iron. The plaque just below the statue says its name Järnpojken ("The Iron Boy"). It was created by Liss Eriksson in 1919.

From the mid 19th to the mid 20th century Gamla stan was considered a slum, many of its historical buildings left in disrepair, and just after World War 2, several blocks together five alleys were demolished for the enlargement of the Parliament. From the 1980s, however, it has become a tourist attraction as the charm of its medieval, Renaissance architecture and later additions have been valued by later generations.

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Cesis Castle

German crusaders known as the Livonian Brothers of the Sword began construction of the Cēsis castle (Wenden) near the hill fort in 1209. When the castle was enlarged and fortified, it served as the residence for the Order's Master from 1237 till 1561, with periodic interruptions. Its ruins are some of the most majestic castle ruins in the Baltic states. Once the most important castle of the Livonian Order, it was the official residence for the masters of the order.

In 1577, during the Livonian War, the garrison destroyed the castle to prevent it from falling into the control of Ivan the Terrible, who was decisively defeated in the Battle of Wenden (1578).

In 1598 it was incorporated into the Polish-Lithuanian Commonwealth and Wenden Voivodship was created here. In 1620 Wenden was conquered by Sweden. It was rebuilt afterwards, but was destroyed again in 1703 during the Great Northern War by the Russian army and left in a ruined state. Already from the end of the 16th century, the premises of the Order's castle were adjusted to the requirements of the Cēsis Castle estate. When in 1777 the Cēsis Castle estate was obtained by Count Carl Sievers, he had his new residence house built on the site of the eastern block of the castle, joining its end wall with the fortification tower.

Since 1949, the Cēsis History Museum has been located in this New Castle of the Cēsis Castle estate. The front yard of the New Castle is enclosed by a granary and a stable-coach house, which now houses the Exhibition Hall of the Museum. Beside the granary there is the oldest brewery in Latvia, Cēsu alus darītava, which was built in 1878 during the later Count Sievers' time, but its origins date back to the period of the Livonian Order. Further on, the Cēsis Castle park is situated, which was laid out in 1812. The park has the romantic characteristic of that time, with its winding footpaths, exotic plants, and the waters of the pond reflecting the castle's ruins. Nowadays also one of the towers is open for tourists.