Following the Livonian Crusades in the 13th century, Terra Mariana was established, encompassing modern-day Estonia and Latvia. It was created in 1207 as a feudal principality within the Holy Roman Empire, later becoming directly subject to the Pope in 1215. The region was divided between the Livonian Order, various bishoprics, and the Duchy of Estonia, which was under Danish control.
In 1227, the Sword Brethren, a German crusading order, conquered the last pagan stronghold on Saaremaa. Estonia was ostensibly Christianized, and control was exercised through strategically located castles. Estonia's northern regions (Harjumaa and Virumaa) were under Danish rule until 1346, when Denmark sold its Estonian territories to the Teutonic Order for 19,000 silver marks. This marked the end of Danish sovereignty, and the Teutonic Order absorbed these territories into its control.
A political map of the Medieval Livonia, circa 1260, along with surrounding areas. © Termer
By the 14th century, the Livonian Order dominated most of northern and central Estonia, while the bishoprics controlled the remaining areas. Estonia’s major cities, including Tallinn (Reval), flourished as part of the Hanseatic League. In 1248, Tallinn was granted Lübeck Rights, becoming a key trading hub.
Throughout this period, the local German-speaking nobility established itself as the dominant force in Estonian society, controlling land and urban trade through a network of manorial estates. However, tensions remained high between the local Estonian population and the foreign rulers. One of the most significant uprisings occurred in 1343–1345 during the St. George's Night Uprising, when Estonians rebelled against the German and Danish rulers. The rebellion was suppressed by the Teutonic Order, and its leaders were executed. Following the revolt, Danish territories were sold to the Teutonic Order, consolidating their control over Estonia.
The Livonian Confederation, established in the 15th century, brought together the Livonian Order, the bishoprics, and the cities in a loose political structure. Despite internal strife and external pressures, including invasions from Muscovy in 1481 and 1558, the Germanic elite maintained their dominance. However, by the mid-16th century, the Confederation weakened, leading to its dissolution during the Livonian War (1558–1583).
As a result of the Livonian War, Sweden, Poland-Lithuania, and Denmark divided Estonia and Livonia. Northern Estonia became Swedish Estonia, southern Livonia became part of Poland-Lithuania, and Saaremaa fell under Danish control. This marked the end of medieval Livonia and the onset of Swedish and Polish-Lithuanian rule in Estonia, setting the stage for the region's future conflicts.