Archaeology

Old Oswestry is amongst one of the largest of the Welsh Borders Hill Forts, and is unique in being placed on the plain instead of up in the Hills,  and in the series of deep hollows on the western side whose function is unknown.  Excavations in 1939-1940 suggest that the earliest settlement on the fort dates back to 700BC, with evidence of unfortified, timber-built round houses on top of the natural hill.  Subsequent phases saw successive ramparts built up around the top of the hill, and stone round houses within the enclosure.  This had begun by c600BC estimated from pottery finds.  There are an impressive five ramparts altogether, the earliest are at the top, latest phase at the base. 

The Iron Age began in about 800 to 600 BC, and finished by coalescing to become the Romano-British period after the Roman conquest in AD43.  No evidence exists for Roman occupation of the site,  although the Romans had a strong presence in the area, including the Rhyn Park Marching Camp on the old Roman Road called Watling Street (A5) and in Chirk. The fall of Rome in the 5th century AD had little real effect in the Borders since the Roman army had been dwindling for some time. 

Britain became divided up into smaller kingdoms, and in c500-600 AD the Hill Fort became incorporated into the construction of Wat's Dyke, a boundary marker between the Mercian kingdom and Wales in this area, which runs roughly parallel to the more famous Offa's Dyke on the hills to the west.  

It is likely that the Hill Fort became reoccupied during the Anglo-Saxon Period.  Old Oswestry Hill Fort is likely to be the final stand by King Cynddylan, defeated by Saxon king Oswy in 658AD. (Welsh Annals).