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Archaeologists have found Roman pottery and coins within the modern town centre.
The town was originally known in Welsh as Abermynwy ("mouth of the Monnow"), replaced by Trefynwy ("Monnow town" – the initial m of Mynwy mutating in Welsh to f pronounced /v/) by the 1600s.
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.
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.
After the end of Roman rule in Britain, the area was at the southern edge of the Welsh kingdom of Ergyng.