The town of Dmitrovsk is located at the confluence of the Nerussa and Obsheritsa rivers. In 1711, the Moldovan ruler Dmitrie Cantemir took Russian citizenship and Peter the Great presented his associate with an estate in the then Sevsky district of Government of Oryol.

Cantemir settled Moldavians, Vlachs, Bashkirs and Ukrainian on his vast estate. In 1715, on the order of Kantemir, in the village of Dmitrovka (named after Dmitrie Kantemir), a manor was built with a palace, a park, which is preserved till nowadays, and outbuildings.

In 1721, next to the estate, on the high bank of the river, the construction of the church of Demetrius of Thessalonica began, which at first was the home church of the Kantemirs. The church has become the only one in the Oryol region in Petrine Baroque style. After the death of Dmitrie Kantemir in 1723, the estate in the Sevsky district was successively owned by his sons: Konstantin, Matvey and Sergey.

June 25, 1782 by the decree of Catherine the Great the village was transformed into the city of Dmitrovsk. The Moscow-Kiev tract ran through the city.

Dmitrovsk Historical and Ethnographic Museum has established in 1973.