Kuressaare developed on the shore of the Livonia Bay where ancient islanders had their stronghold and trading place. After the German-Danish conquests in the 1230s the control of Rigas bishop over the island began to strengthen. Near the bishopric castle, erected in the 14th cent. and still there today, the town developed. From 1559-1645, Saaremaa belonged to Denmark and Kuressaare obtained the freedom of a town on 8 May 1563. Many wealthy tradesmen and craftsmen came here during the Livonia War and Kuressaare obtained several trading advantages and privileges. From 1645-1710, Saaremaa was under the Swedish crown and these years marked a rapid economic and social development of the town. From 1646-1650 more than 30 ships from abroad and 60-70 boats from Saaremaa and Kurland entered Kuressaare harbour. Although a small town, Kuressaare had a big merchant marine 3 large ships and several capacious vessels. From 1710-1918, Kuressaare and Saaremaa were a part of the Russian Empire. In 1710 Russian troops set the town on fire, leaving only 5 buildings in Kuressaare. The outburst of plague the same year left only 11 town citizens living in Kuressaare. Kuressaare started developing once again in the 18th cent. During the independence period of 1918-1940 Kuressaare was an internationally recognised health and summer resort. During the Soviet period in 1940-1990 the traditional development of Kuressaare was blocked as Saaremaa became one of the closed areas in Estonia. On 1 October 1990, Kuressaare was the first town in Estonia to re-gain the status of a local authority and since then Kuressaare has again witnessed a rapid development.

Kuressaare today, is a place where you can meet open minded islanders with a friendly sense of humour in the middle of urban culture. In spite of its island location, it is possible to see many features characteristic of mainland cities here. Kuressaare has digital communication lines, a hospital with modern equipment, a new theatre, culture events that attract crowds of people, a good level of services and a beautiful seaside area with a yacht harbour. In contrast to big cities, Kuressaare is a quiet and cosy town with an unpolluted environment and clean drinking water. There is no black smoke from industries and the streets are not overcrowded with traffic.