The Battles at Otepää and Vastseliina

  By Rider, 18 August 2006; Revised 30 August 2006
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By the 13th century, Estonia had been conquered and enslaved by the Germans. There were many attempts of rebellion but one stands out: The Harju Rebellion or the Uprising of Jüriöö (St. George's Night). The Estonians had planned the rebellion to begin on the 30th of April. However the leaders inadvertently began it earlier, on the night of the 22rd of April, so their allies could not come to aid them in time. The rebels managed to gather a large force (up to 25,000 strong some believe), which was split into two parts: the northern and southern forces. The northern army walked to it’s doom at Reval (nowadays Tallinn) where it tried to unsuccessfully siege Reval but was crushed by German nobles. Over 3,000 died. The southern army went to siege Hapsal (Haapsalu). The southern force was supposed to be aided by Pskovians who they were due to rendezvous with at Otepää on the 25th but the Germans got wind that the Pskovians were coming to their aid.
The Battle at Otepää
The southern army had to make it to Otepää on the 25th of May to unite with the Pskovians who had already arrived and were there waiting for them. After crushing the northern army, the Germans sent a large army to the southern front to join southern forces already battling Estonians, with instruction to prevent the two forces uniting.
The Livonian Order’s Brother Dietrich von Rambov was stationed near Kiriempe (Kiräpä). When he was informed of the rebellion, he immediately gathered his knights, brothers and the men of the Bishop of Tartu and decided to attack the Pskovians at Otepää  immediately. He sent a message to the German army position near Otepää that he was going to attack from one side, but the peasant carrying the message was killed by a bear. So the main force couldn't coordinate the attack along with Dietrich. Dietrich, oblivious to this, still attacked the Pskovians. Brother Johan de Witte was brave and assaulted the enemy along with landowner Johan van Levenwolde who commanded the troops of the Bishop. They killed many Pskovians but were ultimately destroyed. Johan van Levenwolde and Brother Johan de Witte died along with 14 Germans and ten Brothers.
After the assault the Pskovians retreated towards Vastseliina, an alternative river crossing point to link up with the Eastonians by a different route. In five days they covered an area of approximately 80 leagues while regarding against the closely pursuing the Germans.
The Battle at Vastseliina
Dietrich von Rambov continued to try to stop the Estonians from uniting with the Pskovians. Their plan was as follows: the Grand Master Dreylöven would gather the German main forces near Otepää while Dreylöven maintain connection with Northern Estonia through Lake Peipsi (Peipus). Dietrich von Rambov went to Vastseliina and covered the most direct way to Pskov.
The retreating Pskovians reached Vastseliina and tried to cross a river, but a German cavalry unit had blockaded it. Then the German garrison of Vastseliina sortied out to attack the Pskovians who were forced into battle.
Unfortunately, to explain the events, we must put our trust in the Chronicles of Pskov that exaggerate battle's description. The Chronicles say that the retreating Pskovians managed to order themselves so that they decisively defeated the Germans coming from Vastseliina. The battle was very difficult - that much is clear. A large force of the Pskovians ran into the forests and did not take part of the battle at all. The army that had retreated for five days, supposedly lost seventeen men in the fierce battle against the garnison of Vastseliina.
Another interesting fact is that the Pskovians reached Pskov two days after the battle even though they had to march for more than 80 leagues. The number of participating combatants is also questioned: The Chronicles of Pskov suggests that about 5,000 soldiers took part of the Battle at Vastseliina. A German chornicler tells us that over 1,000 Pskovians fell at Vastseliina along with two German commanders, two Brothers and fourteen nobles. The number of infantry that fell is unmentioned, a common literary occurrance in the Chronicles of Renner. So what force could lose 1,000 men if the Pskovians lost only 17? Even the Pskovian commanders sent out messages for help.
A possible answer may be found in the Chronicles of Novgorod which mentioned that 5,000 men retreated from Northern Estonia to Ostrov. The Estonians wanted to unite with Pskovians but the Germans in the south prevented them from uniting. The Estonian army however, realizing what was at stake attacked the Germans with all their forces and the Germans attacked the Estonians whilst the Pskovians were gathering. The Estonians were encircled but they broke out and retreatrd back towards Ostrov. The Germans dared not go after them because Lithuanians had come to Northern Latvia and the Estonian main forces had escaped.
It can be said that the Estonian intelligence was good enough to counter the German's, to help the Pskovians escape complete annhiliation and still distrupt the Germans from communicating with each other.
The Continuing Rebellion
The Rebellion continued for two years when the saarlased were finally destoryed. By 1345, much of the Estonian population had died  and the German numbers had lessened too.
’Eesti vabadusvõitlus 1343-1345’ by Juhan Luiga; Tallinn: Varrak, 1924