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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.
Initially it would have been a motte and bailey castle, later rebuilt in stone, and refortified and developed over time.
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).