Henry I, Duke of Brabant, founded this city when he was about 20 years old. His family had owned a large estate at nearby Orthen for at least four centuries, and in 1185 - the traditional date; the first contemporaneous mention is 1196 - he granted city rights to a new settlement on a wooded sand dune in the middle of a marsh. The setting was the point. He wanted a fortress against encroachment from Gelre and Holland, and the surrounding swamp was natural defense. The city was destroyed in a joint Gelre-Holland expedition in 1203 and quickly rebuilt. By the 14th century a much larger wall had gone up, with the rivers Dommel and Aa diverted into artificial channels to form a moat. The swamp around the walls would be Den Bosch's secret weapon for the next 400 years - any besieger trying to surround the city ended up trying to surround water, and the defenders could flood huge areas at will.

Jheronimus van Aken - the painter the world calls Hieronymus Bosch - was probably born here around 1450 and almost certainly died here in 1516. His name on his paintings was a contraction of city and given name, and his work - tortured saints, fantastical demons, cities on fire, fish swimming through air - is unlike anything that came before or after in the late Northern Renaissance. He grew up when Den Bosch was, after Utrecht, the second-largest population center in what is now the Netherlands. The city was also a serious center of music: composers like Jheronimus Clibano trained at its churches, Matthaeus Pipelare ran the music for the Confraternity of Our Lady, and the Habsburg court copyist Pierre Alamire did much of his work here. The house where Bosch worked still stands on the central market square and can be visited. The Jheronimus Bosch Art Center, dedicated to his work, occupies a deconsecrated church a short walk from his studio.

When the Eighty Years' War turned the Low Countries into a religious battlefield, Den Bosch chose the Habsburg Catholic side and thwarted a Calvinist coup. Prince Maurice of Orange besieged the city in 1601 and again in 1603 and failed both times. By the renewed fighting after 1618 the fortifications had been so greatly expanded that the city earned a nickname: moerasdraak, the Swamp Dragon. It was deemed impregnable. In 1629 Maurice's brother Frederick Henry decided to take it anyway, and the stratagem he used became legendary in military engineering. He diverted the Dommel and Aa rivers entirely. He built a 40-kilometer dyke. He created a polder around the city by pumping out the water with windmills. After three months of siege, Den Bosch surrendered. The Republic treated the captured territory as an occupation zone without political liberties for decades afterward - the local Catholics, who would not regain equal rights until the 1795 Batavian Republic, lived in the same houses as before under a different flag.

The Sint-Janskathedraal dominates the central square and has done so since around 1220. Its style is Brabantine Gothic, with the soaring verticality and skeletal stonework that mark the late medieval Low Countries' answer to French Gothic. What makes it strange and beloved are the small stone figures - sculpted craftsmen and saints and demons and ordinary medieval people - perched along almost every arch and rim of the exterior. They look like they are working, climbing, watching the square below. A long restoration finished in 2010 reversed years of acid rain damage and wear. The 14th-century town hall on the same square got a new Dutch Baroque facade after the 1629 conquest, a visible mark from the new Protestant masters. Across the square stands De Moriaan, the oldest remaining brick house in the Netherlands, built in the early 13th century. In 1956 the city council wanted to demolish it for traffic access; the national government refused the permit, and instead the building was restored starting in 1963 - the first sign of the preservation politics that would soon save the underground Binnendieze too.

From January 1943 to September 1944 the Germans operated a concentration camp complex near Vught, a village a few kilometers south of Den Bosch. They called it Herzogenbusch; the Dutch call it Kamp Vught. About 31,000 people were imprisoned there over those 20 months, of whom roughly 12,000 were Jewish. The site is now a memorial. Den Bosch itself was liberated between 24 and 27 October 1944 by British soldiers of the 53rd (Welsh) Infantry Division under Major-General Robert Knox Ross, after the 1st Battalion of the East Lancashire Regiment fought through resistance on 23-24 October. The old city survived the war relatively intact - the geography that had protected it from sieges also kept it from the rigorous postwar reconstruction that flattened parts of Rotterdam and Eindhoven. Today the historic center of Den Bosch is one of the most complete medieval cityscapes in the Netherlands. The carnival celebrations every February rename the city Oeteldonk for three days, in a tradition formalized between 1881 and 1883, and the whole population dresses in farmers' smocks and red-white-yellow scarves and pretends, with great enthusiasm, that the duke's forest has temporarily become a village in a marsh.