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The city's official name is a contraction of the Dutch des Hertogen bosch-"the Duke's forest". The duke in question was Duke Henry I of Brabant, whose family had owned a large estate at nearby Orthen for at least four centuries. He founded a new town located on some forested dunes in the middle of a marsh. At age 26, he granted 's-Hertogenbosch city rights and the corresponding trade privileges in 1185. This is, however, the traditional date given by later chroniclers; the first mention in contemporaneous sources is 1196. The original charter has been lost. His reason for founding the city was to protect his own interests against encroachment from Gelre and Holland; from its first days, he conceived of the city as a fortress. It was destroyed in 1203 in a joint expedition of Gelre and Holland, but was soon rebuilt. Some remnants of the original city walls may still be seen. In the late 14th century, a much larger wall was erected to protect the greatly expanded settled area. Artificial waterways were dug to serve as a city moat, through which the rivers Dommel and Aa were diverted.

The birthplace and home of one of the greatest painters of the northern Renaissance, Hieronymus Bosch, 's-Hertogenbosch suffered a catastrophic fire in 1463, which the then (approximately) 13-year-old Bosch probably witnessed; presumably, this fire provided inspiration for the fiery hell-scapes that would later make Bosch famous.

Until 1520, the city flourished, becoming the second largest population centre in the territory of the present Netherlands, after Utrecht. The city was also a center of music, and composers, such as Jheronimus Clibano, received their training at its churches. Others held positions there: Matthaeus Pipelare was musical director at the Confraternity of Our Lady; and renowned Habsburg copyist and composer Pierre Alamire did much of his work at 's-Hertogenbosch.

's-Hertogenbosch was founded as a fortified city and that heritage can still be seen today. After World War II, plans were made to modernise the old city, by filling in the canals, removing or modifying some ramparts and redeveloping historic neighbourhoods. Before these plans could come to effect however, the central government declared the city a protected townscape. Most historic elements have been preserved. Because the main ramparts are crucial in keeping out the water, they have never been slighted, their usual fate in the Netherlands. In contrast to cities like Rotterdam, 's-Hertogenbosch also survived the Second World War relatively unscathed. Much of its historic heritage remains intact, and today there are always renovations going on in the city to preserve the many old buildings, fortifications, churches and statues for later generations. In 2004 the city was awarded the title European Fortress City of the year. It is planned to restore the city defences to much of their old glory in the coming years. 's-Hertogenbosch also has the oldest remaining brick house in the Netherlands, 'de Moriaan', which was built at the beginning of the 13th century. In the 1960s, de Moriaan was renovated to its former glory based on a famous 16th-century Dutch painting called 'De Lakenmarkt van 's-Hertogenbosch' ('The fabric market of 's-Hertogenbosch').[ In the north of the old city, the hexagonal powder arsenal, or Kruithuis, still exists, one of only two of its kind in the country. The Townhall is an originally 14th-century Gothic building, transformed in the typical style of Dutch classicism in the 17th century. Around the city itself many other fortresses can still be seen. Until recently it was a major garrison town.

The old city of 's-Hertogenbosch is still almost completely surrounded by continuous ramparts. On the south side, this wall still borders on an old polder, kept intact as a nature reserve, that stretches all the way to Vught. These city walls are currently undergoing renovations. Hidden below the old city is a canal network called the Binnendieze that once spanned 22 km (14 mi). It started out as a regular river, the Dommel, running through the city in medieval times but due to lack of space in the city, people started building their houses and roads over the river. In later times it functioned as a sewer and fell into disrepair. In recent decades, the remaining sixth of the old waterway system has been renovated, and it is possible to take several guided subterranean boat trips through it.

's-Hertogenbosch is also home to Saint John's Cathedral (Sint Jans kathedraal in Dutch), which dates from c. 1220 and is best known for its Brabantine Gothic design and the many sculptures of craftsmen that are sitting on almost every arc and rim along the outside of the cathedral. In 2010 an extensive restoration was completed, undoing the damage of many years of wear-and-tear and acid rain.

Museums are the Stedelijk Museum 's-Hertogenbosch, Noordbrabants Museum, Jheronimus Bosch Art Center and Museum Slager. The painter Hieronymus Bosch (c. 1450-1516) remains probably the best known citizen of 's-Hertogenbosch.

The city is also the location of the Bolwoningen complex, an array of fifty experimental spherical houses designed by Dries Kreijkamp.