Kuressaare first appeared on maps around 1154. The island of Saaremaa (German, Swedish: Ösel) was conquered by the Livonian Brothers of the Sword under Volkwin of Naumburg in 1227, who merged with the Teutonic Knights shortly afterwards. The first documentation about the castle (arx aquilae) has been found in Latin texts written in 1381 and 1422. The city around the fortress flourished after its building. It became the see of the Bishopric of Ösel-Wiek established by Albert of Riga in 1228, part of the Terra Mariana.Johann von Münchhausen, bishop since 1542, had turned Protestant. With the advance of the troops of Tsar Ivan IV of Russia in the course of the Livonian War, he sold his lands to King Frederick II of Denmark in 1559 and returned to Germany. Frederick sent his younger brother Prince Magnus to Kuressaare where he was elected as bishop in the following year. From him the city obtained its civic charter, modeled after that of Riga in 1563. The bishopric was finally secularised in 1572 and Kuressaare fell to the Danish crown.
In 1645, it passed to Swedish control by the Treaty of Brömsebro after the Danish defeat in the Torstenson War. Queen Christina of Sweden granted to her favourite Magnus Gabriel de la Gardie the title of a Count of Arensburg, the German and Swedish name by which Kuressaare was known at that time. The city was burnt to the ground by Russian troops in 1710 during the Great Northern War and suffered heavily from the plague. Abandoned by the Swedish it was incorporated into the Governorate of Livonia of the Russian Empire with the 1721 Treaty of Nystad.
During the 19th century Kuressaare became a popular seaside resort on the Baltic coast. During World War I (between September and October 1917), German land and naval forces occupied Saaremaa with Operation Albion. During World War II, the Battle of Tehumardi took place. In October 1990, Kuressaare was the first town in Estonia to regain its self-governing status
