[2] The whole area of the district belongs to the drainage basin of the Sozh River, a tributary of the Dnieper.

The rivers in the northern, central, and western parts of the district flow into the Vikhra, whereas those in the eastern and the southern parts belong to the drainage basins of other right tributaries of the Sozh.

Between second half of the 14th century and the middle of the 17th century, the area belonged intermittently to the Grand Duchy of Lithuania, to Poland, and to the Grand Duchy of Moscow.

On 3 March 1924, a half of Mstislavsky Uyezd was transferred to Byelorussian Soviet Socialist Republic, and seven volosts were left in Smolensk Governorate.

[9] On 12 July 1929, governorates and uyezds were abolished, and Monastyrshchinsky District with the administrative center in the selo of Monastyrshchina was established.

On August 1, 1930 the okrugs were abolished, and the districts were subordinated directly to the oblast.

A road of a poor quality connects Monastyrshchina with Mstsislaw across the border with Belarus.