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Otepää and its surroundings has greatly suffered due to the activities of the hostile troops. This started from the times of ancient fight for freedom, then from settling of relations between the bishopric and German order at the end of XIV century when the bishop castle having located on Linnamäe in Otepää was burned.

The destruction activities continued during the Northern War up to in 1702 the whole surrounding of Otepää was plundered by the Russian troops and both the church and pastorate building were burned. The August days of 1944 became tragic for Otepää when most of the then city of Otepää was destroyed as the joint company of the fighting parties. According to the memories spreading around folk the walnut forest covered the highland under the current city of Otepää ("Nusstage" in German).

When in 1862 the small town got the licence permit, this was also blessed with the name of Nuustaku which was replaced with the historical name of Otepää only 60 years later (1922).

Otepää bears the name of the city from 1 April 1936, today about 2500 people live here. The citizens of Otepää have introduced themselves as the ones fond of education through the ages. The first folk school started its activities here in 1686 when one of the successors of B. G. Forselius Tartu seminar was employed here.

The first parish school in Estonia was established in Kanepi in 1805. The substantial activity as well as the economic situation of the schools of Otepää parish improved considerably during the period of activities of Jakob Hurt who worked in Otepää as the minister in 1872-1880. When working here Jakob Hurt wore two titles of the president - in the Estonian Society of Writers and in the chief committee of foundation of Aleksander school in Estonia. He created the master plan for collecting the folk poetry and started to realise it.

During the 7-8th centuries the already permanently founded stronghold was established on the southern higher part of the hill. The opening settlement was erected on the northern lower plateau which during the years also expanded to the north-eastern foothill of Linnamäe.
Approximately in the middle of the 11th century many current strongholds in Estonia were left behind and new were established though in other places. Otepää stronghold was one of the few which remained to exist and were even more fortified. Otepää stronghold is the third settled point of Estonia which is mentioned in the chronicles of Old Russia, i.e. "leetopiss" (Tartu stronghold is mentioned in 1030 and Keava stronghold in 1054).





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