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Ivan Kalita presented his part of the town to the boyar Rodion Nestorovich, who presently wrested the other part from Novgorod. In 1345, Simeon the Proud gave Volokolamsk to his father-in-law, one of Smolensk princes. While in possession of Smolensk, the town withstood a siege by Algirdas during the Lithuanian–Muscovite War (1368–72). Vladimir the Bold defeated Tokhtamysh near Volokolamsk in 1383. Soon thereafter, it reverted to Novgorod. The town remained the southernmost enclave of the Novgorod Republic until 1398, when Vasily I definitively incorporated it into the Grand Duchy of Moscow. Ten years later, it was granted for two years to Švitrigaila, who had just defected to Moscow. Having lost its Hanseatic trade and connections with Novgorod, the town declined and was not mentioned by any sources for the next half a century. It was in 1462, when Volokolamsk was given by Ivan III to his younger brother, that the town became the seat of a full-scale appanage principality. Its first prince erected the single-domed limestone Resurrection Cathedral, which still stands. Another prince was Andrey Volotsky; the chief monument from his reign is the three-domed cathedral of the Vyazmischi Cloister (1535).
In 1613, Volokolamsk braved a siege by Sigismund III Vasa, an event which led to the town's fortifications being represented on its coat of arms. By that time, Volokolamsk had been associated primarily with the Joseph-Volokolamsk Monastery, situated 17 kilometers (11 mi) to the northeast.
The Soviet authority in Volokolamsk was established in late October 1917. During World War II, a number of violent clashes between the German and Soviet troops and partisans took place near Volokolamsk. The town was under German occupation from 27 October to 20 December 1941, when it was liberated by the 331st Rifle Division.
Alexander Bek's 1944 novel, Volokolamsk Highway («Волоколамское шоссе»), is a lightly-fictionalized account of the defensive fighting by elements of the 316th Rifle Division along the road from Volokolamsk to Moscow in October 1941.
The online game War Thunder (where one controls Armored vehicles such as Tanks) features a ground forces map titled "Volokolamsk", and a larger version titled "Surroundings of Volokolamsk". The map is derided from players as being too open and being too big.[11]
Volokolamsk landfill
In Volokolamsk, there is a controversial landfill. Many protests have occurred over it as the landfill has given many people respiratory problems. The Russian authorities have not yet done anything about the problem.[12]
Губернатор Московской области. Постановление №123-ПГ от 28 сентября 2010 г. «Об учётных данных административно-территориальных и территориальных единиц Московской области», в ред. Постановления №252-ПГ от 26 июня 2015 г. «О внесении изменения в учётные данные административно-территориальных и территориальных единиц Московской области». Опубликован: "Информационный вестник Правительства МО", №10, 30 октября 2010 г. (Governor of Moscow Oblast. Resolution #123-PG of September 28, 2010 On the Inventory Data of the Administrative-Territorial and Territorial Units of Moscow Oblast, as amended by the Resolution #252-PG of June 26, 2015 On Amending the Inventory Data of the Administrative-Territorial and Territorial Units of Moscow Oblast. ).
Московская областная Дума. Закон №1/2005-ОЗ от 11 января 2005 г. «О статусе и границах Волоколамского муниципального района и вновь образованных в его составе муниципальных образований», в ред. Закона №127/2010-ОЗ от 29 октября 2010 г. «О внесении изменений в Закон Московской области "О статусе и границах Волоколамского муниципального района и вновь образованных в его составе муниципальных образований"». Вступил в силу со дня официального опубликования. Опубликован: "Ежедневные Новости. Подмосковье", №20, 4 февраля 2005 г. (Moscow Oblast Duma. Law #1/2005-OZ of January 11, 2005 On the Status and the Borders of Volokolamsky Municipal District and the Newly Established Municipal Formations Comprising It, as amended by the Law #127/2010-OZ of October 29, 2010 On Amending the Law of Moscow Oblast "On the Status and the Borders of Volokolamsky Municipal District and the Newly Established Municipal Formations Comprising It". Effective as of the day of the official publication.).