Monastyrshchina (Russian: Монастырщина, Polish: Monasterszczyzna) is an urban locality (a settlement) and the administrative center of Monastyrshchinsky District of Smolensk Oblast, Russia.

It is located on the left bank of the Vikhra River, in the western part of the oblast.

[2] 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.