It was founded in the late 14th century by Vladimir the Bold and named Yaroslavets after his son Yaroslav. In 1485, the town was annexed by the Grand Duchy of Moscow and renamed Maloyaroslavets to distinguish it from Yaroslavl. During the French invasion of Russia, the Battle of Maloyaroslavets took place near this town on October 12 (24) of 1812. The battle was commemorated by a roomy cathedral built at the Black Island (Chyornoostrovsky) Convent of Maloyaroslavets by 1843.