It was founded in 1339 by Ivan Kalita. Since then it has always been the administrative centre of the nearby area. Now it's the centre of Serpukhovsky region(the sub-division of oblast').
The town is situated in the south of Moscovskaya oblast' ( Moscow region, the larger sub-division of the country) so it used to be the military outpost in the time of the Golden Horde. It's history has some relation to the Kulikov battle, the turning point in the history of Russia under the Golden Horde; Boris Godunov's march of 1598 forced to acknowledge him as the Tsar of Russia in the Tatar influential circles.
After the October Revolution of 1917 the monks were turned out by the Bolsheviks. The Monastery was transferred into the quarters for the Latvian Riflemen. After 1931 the Monastery was turned into a prison where massive executions were carried out.
The site of the Cathedral of Saint Anne's conception.
The town itself looks untidy and poor. Whereas, for example, Uglich gives the impression of an 18-19th century town with its cleanliness and relaxed way of life, Serpukhov seems to be the town of the 80s 20th century with characteristic of that time abject poverty, lack of good service and prospects for the future.
Check out where to stay in Serpukhov in order not to get too much disappointed.