The earliest written record mentioning Kuressaare castle is from the 1380s, when the Teutonic Order began its construction for the bishops of Ösel-Wieck.

From the outset, it was a stronghold belonging to the bishop of Saare-Lääne (German: Ösel-Wiek) and remained one of the most important castles of the Bishopric until its dissolution during the Livonian War.

Following the Peace of Brömsebro, which ended the 1643-1645 war between Sweden and Denmark-Norway, Saaremaa passed into Swedish hands.

Following the Great Northern War, Saaremaa and Kuressaare castle became a part of the Russian Empire.

[4] As the frontiers of the Russian Empire gradually pushed further west, Kuressaare lost its strategic value.

[4] The fact that Kuressaare castle was not employed by the armies who fought in the Crimean War is also indicative of its lost strategic importance.

When the Russian garrison left the fortress in 1711 following the Great Northern War, they deliberately blew up much of the fortifications and the castle, but later restored some of it.