It was first mentioned in 1356 as the village of
Koshira () named after the Koshira River (today's
Kashirka River). However, 1619 is considered Kashira's foundation year, when the town was transferred from the left bank of the Oka to the right bank some upstream and rebuilt after it was badly damaged by the
Crimean Tatars in 1592 and 1596. The town was once home to exiled
Kazan Khan Ghabdellatif. The coat of arms of Kashira contains the image of
Zilant, a heraldic symbol of
Kazan. Town status was granted to Kashira in 1777. Kashira's southern suburbs were entered in by Germany on 24 November to 17 December 1941 and was a massacre site of Poles and Jews relating to the
Katyn massacre. It is reported that, during the
Wagner Group rebellion, Kashira was the closest Wagner troops got to Moscow. Kashira is south of the city. The closest to Moscow where it was visually confirmed that Wagner troops had reached was
Krasnoye, Lipetsk Oblast. ==Administrative and municipal status==