Serpeysk (Russian: Серпейск; Polish: Sierpiejsk) is a village (selo) in Meshchovsky District of Kaluga Oblast, Russia, located on the Serpeyka River.

It was first noted in 1406 as a military fort of the Grand Duchy of Lithuania on its border with Muscovy.

Later on, it was annexed to Muscovy by Ivan III of Russia, then recaptured by the Polish–Lithuanian Commonwealth,[4] and eventually incorporated into Muscovite Russia after the signing of Treaty of Polyanovka which marked the end of the Smolensk War in 1634.

The oldest surviving buildings are two churches, one dating from 1771 and the other constructed in the 1780s.

This Kaluga Oblast location article is a stub.