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[[File:Памятник 400-летию Орла.jpg|thumb|right|A monument of 400th birthplace anniversary (photo 2016)]]
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While there are no historical records, archaeological evidence shows that a fortress settlement existed between the [[Oka River]] and [[Orlik River]]s as early as the 12th century, when the land was a part of the [[Principality of Chernigov]]. The name of the fortress is unknown; it may not have been called Oryol at the time. In the 13th century, the fortress became a part of the [[Zvenigorod]] district of the [[Karachev]] Principalinsty. In the early 15th century, the territory was conquered by the [[Grand Duchy of Lithuania]]. The city was soon abandoned by its population, after being sacked either by Lithuanians or the [[Golden Horde]]. The territory became a part of the [[Tsardom of Russia]] in the 16th century.
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[[Ivan the Terrible|Ivan IV Vasilyevich]] decreed that a new fortress be built on the spot in 1566, for the purpose of defending the southern borders of the country.{{citation needed|date=June 2010}} The fortress was built quickly, with work starting in the summer of 1566 and ending in the spring of 1567. The location chosen was less than ideal strategically, as the fortress was located on a seasonally flooded low ground easily targeted from the neighboring high ground. [[False Dmitry I]] and his army passed through Oryol in 1605; [[Ivan Bolotnikov]] in 1606; [[False Dmitry II]] camped in Oryol for the winter of 1607–1608. Polish intervention sacked it in 1611 and 1615; the population fled after the second sacking and moved to [[Mtsensk]]. Orlovsky Uyezd nonetheless continued to exist on paper.
Oryol was rebuilt in 1636. The question of moving the fortress to the more advantageous high ground was debated until the 1670s, but the move was never made. The fortress was deemed unnecessary and was taken apart in the early 18th century.
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In the mid-18th century Oryol became one of the major centers of grain production, with the Oka River being the major trade route until the 1860s when it was replaced by a railroad.
Oryol was granted town status in 1702. In 1708, Oryol was included as a part of [[Kiev Governorate]]; in 1719, [[Oryol Province]] was created within Kiev Governorate. The Province was transferred to the newly created [[Belgorod Governorate]] in 1727. On March 11 (February 28 [[Julian calendar|old style]])<!--check date-->, 1778 [[Oryol Vice-Royalty]] was created from parts of [[Voronezh Governorate|Voronezh]] and Belgorod Governorates. In 1779, the city was almost entirely rebuilt based on a new plan; and the Oryol River was renamed Orlik (lit: "little eagle").
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After the [[October Revolution]] of 1917, the city was in Bolshevik's hands, except for a brief period between October 13 and October 20, 1919, when it was controlled by [[Anton Denikin]]'s [[White movement|White Army]].
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Oryol was once again moved between different [[oblast]]s in the 1920s and 1930s (at first as Oryol Governorate until 1928, then [[Central Black Earth Region]] between 1928 and 1934, finally in [[Kursk Oblast]]), finally becoming the administrative center of its own Oryol Oblast on September 27, 1937.
The [[Oryol Prison]] was a notable place of incarceration for political prisoners and war prisoners of the [[World War II|Second World War]]. [[Christian Rakovsky]], [[Maria Spiridonova]], [[Olga Kameneva]] and 160 other prominent political prisoners were shot on September 11, 1941 on [[Joseph Stalin]]'s orders in the [[Medvedev Forest massacre]] outside Oryol.
During the German-Soviet war, Oryol was occupied by the [[2nd Panzer Army|Guderian's Panzer group]] of the [[Wehrmacht]] on October 3, 1941, burst from the south-west.
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