Caerwent was founded in AD 75 as Venta Silurum ("Market town of the Silures") by the Romans to serve as a market town for the Silures, a warlike tribe that had been fighting the Romans since the Roman conquest of Britain. In the early 100s, the forum, baths, shops, and basilica (the center of local government) were built, as well as farms and houses. A temple dedicated to Mars or the Celtic god Ocelus was also built, and a bowl with a chi-ro symbol shows that Christianity was present in the early 200s. In the mid-300s, stone walls were built, and a small garrison may have been present. A polygonal angle-tower dates to this time. The site was occupied after the Romans left, and Christianity grew prevalent enough that it may have become the center of a bishopric. Saint Tatheus founded a monastery in the 500s, and a cemetery was built around the present church. The Kingdom of Gwent was named after Venta Silurum, and the town was renamed Caer-went ("The fortress of Gwent"). The semi-legendary king Caradog Freichfras is believed to have moved his court to Portskewett in the 500s, but the capitol soon returned to Caerwent.

          According to William Caxton, Sir Thomas Malory's publisher, Camelot was in Wales, and according to Chretien de Troyes, Camelot was a short distance from Caerleon. Malory could have derived Winchester from Caerwent, as both of the cities were named "Venta" (in Winchester's case, Venta Belgarum). Alternatively, Malory could have used Winchester as an English translation of the Welsh Caerwent. If Arthur were to be the King at Caerwent, then Caradog could have inherited it from him after the Battle of Camlann. In favor of the theory is the church, which has a number of burials from the 300s to 800s and is dedicated to St. Stephen, as the cathedral of Camelot was supposed to have been.

 
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