Serpukhov was first mentioned in a document of Grand Prince Ivan I Kalita of Moscow, which lists his lands. There is some uncertainty surrounding the date of this document, but the official date is taken to be 1339, just before Prince Ivan's fourth journey to the Golden Horde. This year is considered the official founding date of Serpukhov. Andrey Ivanovich became the first Prince of Serpukhov in 1341 when his father, Ivan Kalita, gave him Serpukhov along with other cities as an appendage. Prince Andrey Ivanovich died in 1358 of the Black Death and was succeeded by his son Prince Vladimir Andreevich of Serpukhov
Prince Vladimir the Brave of Serpukhov
Vladimir Andreevich was just a minor when he became prince and was raised under the guardianship of Metropolitan Alexius (Aleksiy), along with his cousin Dmitri Ivanovich (later known as Dmitri Donskoy) who was also a minor. During Metropolitan Alexius' regency in Serpukhov he established the Vladychny Monastery there in 1360. Metropolitan Alexius taught Vladimir to respect and obey his more senior cousin and this forged a close relationship between the princes. Vladimir became a strong ally of Dmitri Donskoy in his adult years and helped to strengthen the Grand Principality of Moscow, in contrast to the usual Ryurikid fraternal battles. Vladimir Andreevich fought alongside Dmitri Donskoy in the battle of Kulikovo Field in 1380 for which he earned the sobriquet 'The Brave'. Shortly afterwards, in 1382, Khan Tokhtamysh of the Golden Horde led his troops on a raid of Rus lands and sacked Serpukhov, possibly as personal revenge against Vladimir the Brave.
Rule of the Sons of Vladimir the Brave
Prince Vladimir of Serpukhov died in 1410 and his lands were split between his sons. Ivan Vladimirovich became Prince of Serpukhov but died a decade later in 1422. He was succeeded by the short reigns of his brothers Simeon and Andrey, who both died in 1426 from the plague which was ravaging Russian lands at the time.
Liquidation of the Serpukhov Principality
Serpukhov was eventually inherited by Vasili Yaroslavich, a grandson of Vladimir the Brave, in 1427. Vasili was a faithful ally to Grand Prince Vasili II of Moscow, especially during the latter's struggle again Dmitri Shemyaka. During his reign, Vasili Yaroslavich was able to reunite all the land held by his grandfather. However his growing authority and his close relations with Poland-Lithuania caused Grand Prince Vasili II to be suspicious. Vasili Yaroslavich was arrested and exiled to Uglich in 1456 and the Serpukhov Principality was liquidated. In 1462 Vasili Yaroslavich was further exiled to Vologda where he died in 1483.
Crimean Tartar Raids and Serpukhov Kremlin
The start of the 16th Century was marked by the increasing threat posed by the Crimean Khanate who increasingly launched raids on Moscow. Serpukhov was on route from Crimea to Moscow and was important for the city's defence. In 1521 Khan Mehmed I Geray of Crimea's forces raided Moscow and destroyed Serpukhov on the way. To strengthen the city's defensives Grand Prince Vasili III of Moscow ordered that Serpukhov's wooden fortress be replaced with a stone kremlin which was completed in 1556. In 1571 the forces of Khan Devlet I Geray of Crimea defeated Russian forces outside Serpukhov and marched onwards to burn down Moscow. Serpukhov again fell victim to Crimean Tatar raids in 1572 and 1581. In 1598 Tsar Boris Godunov led his troops to face invading Crimean Tatars head on. He set up camp in the Vladychny Monastery. The show of strength resulted in the Crimean Tatars retreating. As a sign of gratitude Boris Godunov made generous donations to the Vladychny Monastery.
Time of Troubles
During the Times of Troubles the people of Serpukhov accepted the First False Dmitri in 1605 who set up camp near the Vladychny Monastery. In 1606 the city then welcomed Ivan Bolotnikov during his uprising. Tsarist troops took control of the city again in 1607 and used it as a base to defeat the nearby insurgents. To show gratitude for the victory Tsar Vasili Shuisky donated the Icon of Tsarevich Dmitri to the Vladychny Monastery. In 1610 the city was occupied by Polish-Lithuanian interventionists who burned much of the city. In 1613 Serpukhov lands were raided by the Nogai and then in 1618 the city was burned by Hetman Petro Sahaidachny and his Cossacks, who were however unable to breach the Kremlin's defences. All this took a great toll on Serpukhov and much of the city was destroyed and required rebuilding.
In 1708 Serpukhov became part of the newly-established Moscow Governorate. Throughout the next two centuries Serpukhov became an important centre of Russia’s textile industry. In 1781 the city was granted a new coat of arms bearing a peacock. The design came about after a questionnaire was sent out for information. The designer was inspired by a message about how at one of the city’s monasteries peacocks are bred.
The Inexhaustible Chalice Icon
In 1878 a peasant whose drinking had led to him losing the use of his legs had a dream that he should go to the Vladychny Convent in Serpukhov and pray to the Inexhaustible Chalice Icon. After seeing this dream a third time the peasant went to the convent only to be told there was no so icon. However after a search of passages in the convent the icon was found. The man prayed as he was told in his dream and not only regained the use of his legs but also completely lost his appetite for alcohol. The icon is now said to help those suffering from alcoholism.
The Soviet period brought many changes to Sepukhov, especially to its monasteries. In 1919 the Vladychny Convent was closed and became a military aviation school up to 1978 until it was abandoned completely. During this time the Inexhaustible Chalice Icon was lost, although copies did survive. The Icon of Tsarevich Dmitri was transferred to the Serpukhov History and Art Museum. The Convent was returned to the Church in 1995. The Vytostsky Monastery suffered a similar fate; in 1918 it was used as the barracks for a company of Latvian Riflemen. It was subsequently used as barracks, warehouses, communal housing garages and even an enclosure for livestock. The monastery was returned to the Church in 1991. The Kremlin also did not survive the Soviet period. Already in a ruined state by the 20th Century, in 1934 the Bolsheviks decided to complete demolish the ruins of the kremlin so that the stone could be used in building the Moscow Metro. Only fragments survive.