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Pskov is one of the oldest cities of Russia, and has been of considerable importance in the history of Russia and the Russian Orthodox Church.

The earliest mention of the city, originally known as Pleskov, comes in 903. At that time, Igor of Kiev married a local noblewoman who was later canonized as St. Olga. The first prince of Pskov was St. Vladimir's younger son Sudislav. During the 12th and 13th centuries, the town was politically attached to the Novgorod Republic. In 1241, Pskov was taken by the Teutonic knights, but St. Alexander Nevsky liberated it several months later. In order to secure their independence, the Pskovians elected a converted Lithuanian prince, named Dovmont (St. Dovmont/Timothy), as their prince in 1266. Having fortified the town, Dovmont defeated the knights at Rakovor. His relics and sword are preserved in the ancient kremlin, and the core of the citadel erected by him is still referred to as "Dovmont's town". By the 14th century, Pskov functioned as the capital of a sovereign republic whose most powerful political force was the merchant class who brought the town into the Hanseatic league. Pskov's sovereignty was formally recognized by Novgorod in 1348. The resulting Pskov Charter was a principal source for the all-Russian law code issued in 1497.

For greater Russia, Pskov was a bridge with Scandinavia and western Europe. As a western outpost of Russia, it was subject to numerous attacks throughout its history. The kremlin withstood 26 sieges during the 15th century century alone. At one point, five stone walls surrounded the city, making it practically impregnable. A local school of icon-painting flourished, and local stonemasons were considered the best in Russia. Many of the unique features of Russian architecture originated in Pskov, and numerous churches and monasteries are located in the city and surrounding countryside.