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On April 28, 2016, by a resolution of the Moscow Regional Duma, Serpukhov was awarded the honorary title "Locality of Military Valor".
In the autumn and winter of 1941, fierce battles were fought on the territory of the Moscow region, on the very approaches to the capital. The front line was very close to Serpukhov. On October 9, the first bombing took place in Serpukhov. In the autumn of 1941, Serpukhov was pitted with anti-tank ditches, built up with barricades, in tense anticipation of another enemy air raid. In 1941, Serpukhov was a frontline city. The front took place near the villages of Troitskoye, Kremenki, Yuryatino – fierce battles were already underway 18 km from Serpukhov. The whole city was then circled by Stalin's words: "Serpukhov should not be surrendered!"
Positions to the west of Serpukhov were occupied by the 49th Army, commanded by Lieutenant General Igor Grigoryevich Zakharkin, after whom one of the streets of Serpukhov is named. German troops encircled the city from the western side at a distance of 6-7 km . The headquarters of the 49th Army was located in the village of Buturlino, which is located east of Serpukhov. Serpukhov was defended by the 60th Division, consisting of the militia of the Leninsky district of Moscow. The pilots of the 178th Aviation Regiment, which was based in the Oka floodplain, near the village of Lipitsy, took part in the defense. This regiment carried out 1,695 sorties, conducted 59 air battles, shot down 22 enemy aircraft, as well as 19 anti-aircraft guns.
The most fierce battles were fought on the Drakino— Kremenki—Pavlovka line. It was only at the end of November 1941 that the German army's offensive was stopped. In mid-November, a counterattack was launched. And the city did not give up.
On December 16, the Soviet troops went on the offensive. After the breakthrough of the German defense, Tarusa and Aleksin were liberated. By January 1942, the front line was moved away from Serpukhov by more than 150 kilometers.
During the war, 597 buildings were destroyed and damaged in Serpukhov, 202 civilians were killed, 317 people were injured. During the initial period of the war, 140 air raids were carried out on the city, 500 high-explosive and 35,000 incendiary bombs were dropped.
Serpukhov has been the southern outpost of the Moscow region since time immemorial. The contribution of the residents and fighters who defended Moscow was highly appreciated – in 1982 Serpukhov was awarded the Order of the Great Patriotic War I degree, and in 2016 was awarded the title "settlement of military valor".