Old Oswestry hillfort was built and occupied during the Iron Age (800 BC to AD 43) and is one of the best-preserved hillforts in Britain. The hill was first occupied in the Neolithic period. The first direct evidence of settlement dates to 1000BC in the Bronze Age when a wooden palisade was built with internal round houses. The impressive main ramparts and entrances visible today were built in four main phases expanding out from top to bottom during the Iron Age. The size of the site and elaborate defences suggests a major tribal centre.
In the 9th-8th century AD the Wat's Dyke rampart and ditch boundary running from Basingwerk in Flintshire through to Maesbury, Shropshire utilised the ramparts of the hillfort as part of its 64km alignment. The dyke probably acts as a Mercian kingdom boundary.
In WWI the interior of the hillfort was used for military training and practice trenches were dug and explosives used to create craters. The poet Wilfred Owen, born nearby, completed his army training here.