Monmouth, United Kingdom

The first recorded settlement at Monmouth was the small Roman fort of Blestium, one of a network of military bases established on the frontiers of the Roman occupation. This was connected by road to the larger Roman towns at Glevum (Gloucester) and Isca Augusta (Caerleon). Archaeologists have found Roman pottery and coins within the modern town centre. During the later Roman period, between the 2nd and late 4th centuries, it appears to have been a centre for iron working, using the local iron ores and charcoal also worked at nearby Gobannium (Abergavenny) and Ariconium (near Ross-on-Wye).

After the end of Roman rule in Britain, the area was at the southern edge of the Welsh kingdom of Ergyng. The only evidence of continuing settlement at Monmouth is a record of a 7th-century church, at an unknown location within the town, dedicated to the Welsh saint Cadoc. In 1056, the area was devastated by the Welsh prince Gruffydd ap Llywelyn, on his way with an army of Welsh, Saxons and Danes to defeat Ralph, Earl of Hereford, and sack the Saxon burh at Hereford, 18 miles (29 km) to the north.

Following the Norman conquest of England in 1066, the Earldom of Hereford was given to William FitzOsbern of Breteuil, Normandy, one of King William's closest allies, who was responsible for defending the area against the Welsh. A new castle was built at Monmouth, holding commanding views over the surrounding area from a sound defensive site and exerting control over both river crossings and the area's important resources of farmland, timber and minerals. Initially it would have been a motte and bailey castle, later rebuilt in stone, and refortified and developed over time. A town grew up around it, and a Benedictine priory was established around 1075 by Withenoc, a Breton who became lord of Monmouth after Roger, the son of William fitzOsbern, was disgraced. The priory may have once been the residence of the monk Geoffrey of Monmouth, who was born around 1100 and is best known for writing the chronicle Historia Regum Britanniae ("History of the Kings of Britain").

The town was recorded in the Domesday Book as part of Herefordshire, and expanded thereafter. There was early burgage development along Monnow Street, and the suburb of Overmonnow, west of the river and protected by a defensive moat called the Clawdd-du or Black ditch, began to develop by the 12th century. Charters from the period refer to the town's trade in iron, and to forges making use of local ore and charcoal. The cinders produced by the forges formed heaps, and were used in building foundations; the name of Cinderhill Street in Overmonnow dates from this period.

During the period of turmoil between the supporters of King Henry III and the barons who sought to curtail his power, the town was the scene of a major battle in 1233, in which the king's forces were routed by the troops of Richard Marshal, Earl of Pembroke. Later, the castle was extended by Henry's son Edmund Crouchback, after he became Earl of Lancaster in 1267. In about 1300, town walls were built, and the Monnow Bridge was fortified. The bridge, now pedestrianised, remains in place, the only such fortified bridge in Britain and reputedly one of only three similar crossings in Europe.

King Edward II was briefly imprisoned at Monmouth Castle in 1326 after being overthrown by his wife Isabella and her lover Roger Mortimer. In the mid 14th century, the castle and town came into the possession of the House of Lancaster through the marriage of John of Gaunt to Blanche of Lancaster. John of Gaunt strengthened the castle, adding the great hall, and the castle became a favourite residence of the House of Lancaster. In 1386, John of Gaunt's grandson was born to Mary de Bohun, in the Queen's Chamber within the gatehouse of Monmouth Castle, while his father Henry Bolingbroke was hunting in the area. The boy was known as Henry of Monmouth before his coronation as Henry V; supported by longbowmen from the area, he won the Battle of Agincourt in 1415. Monmouth's links with Henry are commemorated in the naming of the main town square, Agincourt Square, and in the statue of Henry on the front of the Shire Hall.

From the 14th century onwards, the town became noted for the production of woollen Monmouth caps. The hill of Craig-y-dorth, 1 mile south-west of Monmouth, was the site of a battle in 1404 between Owain Glyndŵr's army and English forces. According to the Annals of Owain Glyn Dwr, "There the English were killed for the most part and they were pursued up to the gates of the town" (of Monmouth). Monmouth, as a border town and administrative centre, suffered after nearby areas, including Usk and Grosmont, were devastated through attacks by supporters of Owain Glyndŵr after the battle and during 1405.