Maloyaroslavets is one of the oldest Russian towns. It is located in the north-eastern part of the Kaluga region, in 60 km from Kaluga and in 120 kilometres from Moscow. Its location at the intersection of the most important roads and its closeness to Moscow historically connected the fate of this small town not only with Moscow, but also with the fate of the Russian state. The first historical document, which mentioned Maloyaroslavets in 1402, was a Spiritual letter by the Grand Prince Vladimir Andreevich the Bold-Donskoy, one of heroes of the Battle of Kulikovo. In the XV century Maloyaroslavets existed under the name of Yaroslavl (in honour of a son of Vladimir the Bold). At the beginning of the XVI century, Moscow Prince Ivan III named it Yaroslavets Maly to make it different from Yaroslavl on Volga. In 1777 the ancient Maloyaroslavets became an uyezd town and a coat of arms was granted to it by a Decree of Catherine the Great: “a silver shield with a crimson toothed border, with a standing bear in the centre of it”, which is related to the name of Yaroslav (the coat of arms of Yaroslavl also depicts a bear).
The battle for Maloyaroslavets was extremely important in the history of the Patriotic War of 1812. The fate of this war resolved in Maloyaroslavets, which has become “the limit for attack, start of escaping and death of the enemy”, as Mikhail Kutuzov put it. There are several monuments devoted to these events in the town. The military and historical museum of 1812 is one of them.
The St. Nicholas Black Island Monastery, unique monument of history and architecture, is located on the outskirts of Maloyaroslavets. A bloody battle for Maloyaroslavets took place near its walls.
There is an ancient settlement, remainders of a fortified Viatichi settlement, within the boundaries of the town. According to territory, it is a hill adjacent to the St. Nicholas Black Island Monastery facing the bank of the Luzha River. The hill has an artificial relatively flat top, which is characteristic for settlements.
During the Second World War, Maloyaroslavets was occupied for a short period of time. The town also severely suffered from fierce battles.
On 7 May 2012, an honorary title “Town of Military Glory” was granted to the town by the decree of the President Vladimir Putin.
The town regularly organises reconstructions of the battle of Maloyaroslavets, which is attended by guests and participants from different countries of the world. In 1992, a Maloyaroslavets Town Picture Gallery named after Yelisaveta Chernyavskaya was opened in the former hospitium of the Black Island Monastery, where along with 70 works of Yekaterina Chernyavskaya, there are 200 other paintings, mainly by regional painters. There is a section of wooden sculptures and a section of decorative and applied arts in the museum.
Starting from 1998, the town has been organising an annual forum of bikers named Motoyaroslavets. The festival was born and grew from the Face to Face motor festival conducted by Moto magazine as a congress of readers of Moto magazine. The festival traditionally takes place in the last weekend on June.