Later Mozhaysk became an important stronghold of the Smolensk dynasty, in the 13th century ruled by Duke (later Saint) Theodore the Black.

A younger brother of the ruling Grand Duke of Moscow usually held the Principality of Mozhaysk - until the practice was dropped in 1493.

In World War II, the German Wehrmacht took Mozhaysk on October  18, 1941;[10]: 157  the Soviet Red Army re-captured it on January 20, 1942.

At that time the wooden statue of Saint Nicholas of Mozhaysk was carved by an unknown master and placed into the cathedral.

The Cathedral of St. Nicholas in the Gothic Revival style, designed by Aleksei Bakarev (Matvei Kazakov's student), started in 1802, but the building was ransacked by the retreating French troops in 1812.

Several bus and marshrutka services operate within Mozhaysk and connect the town with nearby localities, as well as with touristic sites in the fields of Borodino.

109 of the Belorussky suburban railway line, located on the outskirts of the city, serves the adjacement settlement of Stroitel.