Alternate History

Livonian War (St. George's Night)

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Livonian War
Part of St. George's Night
Date 1342 - 1343
Location Livonia
  • Swedish-Estonian victory
  • Power of Livonian Order broken
Estonian rebels

Flag of Sweden Sweden

Flag of Denmark Denmark (1342)

TeutonicOrderFlag Livonian Order

Commanders and leaders
Vesse of Oeselia

Flag of Sweden Dan Niklasson (bailiff of Viborg)

TeutonicOrderFlag Burkhard von Dreileben

Flag of DenmarkBertram von Parembeke

15,000 20,000
Casualties and losses
3000 8000

The Livonian War was a major conflict in the East Baltic, fought between Sweden and allied Estonian rebels and the Livonian Order, initially aided by Denmark. The war, incited by an Estonian uprising, was a Swedish-Estonian victory that established Estonia as a fief of the Swedish crown, under a native aristocracy.


In the Northern Crusades of the 1200s, the pagan tribes of the Baltic had been defeated, subjugated by German and Danish crusaders. Livonia was divided into the Duchy of Estonia, under Danish suzerainty, in the north, and a series of Bishoprics and other smaller polities in the south, under the control of the Livonian Order of Sword Brothers, a knightly society of crusaders. These new rulers proceeded to largely replace the native aristocracy with a foreign one, tax the populace heavily, and undertake abrasive attempts at Christianization. These tensions worsened in the 1340s, as Denmark weakened, resulting in it reducing its garrisons in the region even while increasing taxes.


On St. George's Night (April 23), 1343, a fire was lit on a hilltop in the Central Estonian county of Harria, signalling a coordinated rising across the area. Germans and Danes were brutally killed en masse, with no regard for age or gender. The Estonians renounced Christianity and burned down Padise Abbey, killing 28 monks. The revolt spread to the coast, where the Bishpric of Ösel-Wiek rose in revolt, the capital of which, at Hapsal, was besieged. The main Danish centre in the region, at Reval, was also besieged. The Estonians proceeded to elect four leaders, under whose command they defeated a Danish army under the walls of Reval. Worrying about their ability to withstand the vengeance of the now angered Danes and Livonian Order, the Estonaisn sent a message to the Swedish bailiff of Viborg, offering him Reval if he would send aid. The bailiff agreed, and began gathering a fleet and army, eager for plunder, and an opportunity to gain a strangehold on trade with Novgorod.

The Livonian Order's castle at Paide held out, and was soon deluged with refugees. The Grand Master of the Order, Burchard von Dreileben, sent an Estonian member of the Order to the Estonian camp, asking them to send their leaders to negotiate at the castle. This member promptly betrayed his allegiance, warning them of von Drelieben's true plan: to kill them, leaving the Estonian army leaderless. Now forewarned, the Estonian leaders sent a request for von Dreileben to instead meet them at Reval, which he refused. Negotiations came to an end, and renewed war began.

Swedish and Pskovian Involvement

The Swedish Bailiff of Viborg, Dan Niklasson, had gathered an army of around 10,000 men, along with a substantial fleet, on the Finnish coast. He landed near Reval on 18 May, 1343 and was joined by the bailiff of Åbo a day later. Now blockaded by land and sea, and with no hope of relief, the Danish garrison surrendered, and Reval was duly garrisoned by 150 Swedes. Meanwhile, the greater part of the Estonian army had advanced south. Von Dreileben, having assembled an army at Paide, advanced north to meet them. On 20 May, the two forces met near the town of Kanavere. Although the Estonians, mainly light troops, could not stand against the heavily armoured knights of the Order, they were able to withdraw into a nearby bog, suffering several hundred casualties. Two of the Estonian leaders were killed in the process. The remaining two leaders proceeded to argue over the best course of action; one wanted to surrender, the other to wait for the Swedes' arrival. The latter, Vesse of Oeselia, won out, with his rival killed by soldiers angry at his proposal. In the meantime, the troops of the Order had entirely surrounded the bog, advancing into it on foot.

They were entirely unprepared for the arrival of 5000 Swedish cavalry, who caught the troops of the Order in the rear. Dismounted to fight in the mud, the knights were immobile and ineffective, especially as the Estonians counterattacked. The struggle continued for three brutal hours before the troops of the Order routed. The Swedes and Estonians showed no mercy, massacring the fleeing troops. No more than 1000 of an army of 10,000 survived, with the Grand Master among the dead. The Livonian Order effectively died with him; to assemble the army, he had stripped virtually all of its garrison, leaving its castles vulnerable.

Meanwhile, Estonian envoys had reached the Pskov Republic, telling it of the Order's impending demise and recommending that it take advantage of the opportunity to invade. The Pskovians took notice, and on 28 May, 5000 Pskovians unexpectedly appeared outside the Order's castle of Dorpat on Lake Peipus, sacking it. Others took advantage of the Order's weakness, too. In southern Livonia, the Semigallians and Curonians rose up against the Order, aided by Lithuanian raiders crossing the border from the Grand Duchy of Lithuania.


These rebels sacked the Order's castles at Windau, Goldingen, Ascheraden and Kokenhusen, effectively destroying its control in Courland and Semigalia. Riga, however, held out, repelling Curonian raiders. However, virtually ungarrisoned, the remaining strongholds in Estonia proper quickly fell, particularly as the Swedes, accompanied by Oeselians returning to their ancient practice of seaborne raids, attacked towns all along the coast, even seizing the last Danish stronghold at Narva. Hearing of this, the Danish king, faced with a long, bloody and uncertain campaign to retake his Estonian holdings, offered to concede his rights to them to the Swedish king in return for a payment of 19,000 silver Köln marks, which was accepted.

Fall of Riga and the War's End

The main remaining stronghold of the Order, at Riga, was besieged by the Curonians and Semigalians, who were joined late in the year by an Estonian army under Vesse of Oeselia. An Oeselian fleet also arrived, blockading Riga by sea and taking numerous ships from Denmark and Germany attempting to enter the port. By the end of the year, the city was starving, leading the Archbishop of Riga to expel its civilian population. He, meanwhile, had sent messages to the Teutonic Order and the Hanseatic League, asking for relief and promising extravagant concessions.

Angered at their expulsion, one civilian revealed to Vesse that one of the city's gates was often left unguarded during late hours, due to a lazy guard. That night, several Estonians scaled the walls and opened the gate, after which Riga was subjected to a lengthy and brutal sack, mitigated only by the absence of its population. Only two of the garrison survived; the Archbishop's head was sent to the Grand Master of the Teutonic Order.

Now ensconced at Riga, Vesse toyed with the idea of proclaiming himself King of Livonia. The other leaders of the revolt, however, were unanimously against this, concerned both about the loss of their own power and about the relative weakness of Estonia compared to its neighbours. In the spring, then, Vesse and a delegation of other nobles greeted the returned Bailiff of Viborg and offered Livonia to the King of Sweden as a vassal. Vesse, however, had prepared the ground well, offering his hand in marriage to the Bailiff's daughter, along with a substantial bribe and the cities of Narva and Riga, if he would proclaim Vesse Duke of Livonia. To the nobles' general shock, Vesse was enfeoffed with Livonia as a vassal to the King of Sweden, with other nobles his vassals. Vesse proceeded to eliminate his rivals in a few short months, granting large swathes of Estonia to his allies and supporters as lordships.

Wary, however, of finding themselves with another hostile overlord, the Livonian nobles demanded a confirmation of their privileges from the Bailiff. After correspondence with the King, who was eager to gain such a wealthy fief, this was duly granted. This "Charter of Viborg" granted freedom of religion, considerable self government, and a lightened tax burden to the new Duchy.

The war left Sweden and the new Duchy with several powerful enemies, however. The Teutonic Knights, another knightly order, were eager to avenge the destruction of the Livonian Order. The Hanseatic League, a powerful grouping of mercantile city-states, had lost much of its control over Baltic trade and its privileged position when the towns of Livonia, previously under its influence, were occupied by Estonian and Swedish troops. After the war, Vesse declined to restore these privileges, accusing the League of, not inaccurately, cooperating with the Livonian Order. These tensions would lead to fresh conflicts in the next years

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