Flint castle

Flint was the first castle of what would later become known as Edward I's "Iron Ring". A chain of fortresses designed to encircle North Wales and oppress the Welsh. Its construction began almost immediately after Edward I began the First Welsh War in 1277.
Five years later Welsh forces under the command of Dafydd ap Gruffydd, brother of Llywelyn ap Gruffudd, besieged the castle in an attempted uprising against the English Crown. In 1294 Flint was attacked again during the revolt of Madog ap Llywelyn; this time the constable of the castle was forced to set fire to the fortress to prevent its capture by the Welsh. The castle was later repaired and partly rebuilt.
With the conclusion to the Welsh Wars, English settlers and merchants were given property titles in the new town that was laid out in front of the castle. The plantation borough was protected by a defensive ditch with a wooden palisade on earth banking[10] .[11] Its outline remains visible in streets patterns.[12]
In 1399 Richard II of England was held by Henry Bolingbroke at Flint before being returned to London.
During the English Civil War, Flint Castle was held by the Royalists. It was finally captured by the Parliamentarians in 1647 after a three-month siege. To prevent its reuse in the conflict, the castle was then slighted in accordance with Cromwell's destruction order. The ruins are what remain today.
By the 19th century part of the site's outer bailey was used as Flintshire's County Jail. A quarry also operated nearby.