Written records on Kuressaare date back in 1424. The settlement appeared here as a trading place of ancient islanders and till today the spirit of the Middle Ages can be traced in narrow streets paved with cobblestones and several centuries old hipped roofed houses.

The real pearl of the city is the bishopric castle-fortification from the 14th century, the only one in the Baltic countries surviving in its initial completion. Around the castle, a settlement developed and in 1563 the freedom of a city was granted to the place then called Arensburg. Towards the end of the tsarist time, the Estonian version Kuressaare came into use and the town was officially named so in 1918 when the Republic of Estonia was born.

During the Soviet period the city was called Kingissepa after a red revolutionary who was born here. On 23 June 1988, the city got its historical name back.

Today, the city is next to the mediaeval old town and spa hotels characterised by a charming castle park, pedestrian and cycle paths, health parks, tennis courts, a golf course – much has been done to promote active living. Kuressaare was the first Estonian city to be accepted to the European Healthy Cities Network about 15 years ago.