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The town of Pechory was founded as a posad near a famous Pskovo-Pechersky Monastery in the 16th century and soon developed into an important trading place. During the reign of Ivan the Terrible, Pechory was an important border stronghold. It was besieged numerous times by Russia's enemies: Stefan Batory's forces sacked the settlement during the Siege of Pskov (1581); the Swedes or the Polish stormed Pechory in 1592, 1611, 1615, 1630, and from 1655 to 1657.

After the Great Northern War broke off, Russians renovated the fortifications and Boris Sheremetev began his campaign of 1701 in Pechory. In the 20th century, the settlement that had been in oblivion for centuries, regained its status as a town (1918). From February to December 1918, Pechory was occupied by the Germans. During the Estonian War of Independence, the town was included with the Estonian territories on March 29, 1919. On the grounds of the Tartu Peace Treaty, Pechory and the territory around it, called Setomaa, were given to Estonia.

During the inter-war years, Petseri, as it was called at that time, was the centre of Petserimaa (Petseri County), one of the eleven counties that made up the Republic of Estonia. The St. Peter's Lutheran Church was built in 1926. During World War II the town was occupied by the German Army from August 1941 until August 11, 1944.

In 1945, after Estonia was occupied by the Soviet Union, Pechory and most of Petseri county were transferred to Pskov Oblast of the RSFSR. The territory has remained under Russian control ever since. In 1956, Pechory Secondary School No. 2 was opened for Estonian-speaking pupils.

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