The history of this district in antiquity is not well known, but the closest important Roman settlement was at Catterick in what became known as Rheged, site of the Battle of Catterick. At the terminus of Scandinavian York, there was a local bout of rebellion in Stainmore, which resulted in the death of Eric Bloodaxe. The Scandinavian settlement of this area was eastwards from the Irish Sea with names such as Gilpatrick in Middleham and in Bedale occurring at the time of the Domesday Book. At the time of the Norman Conquest it was the Fee of Gillingshire, held by Edwin, Earl of Mercia. Gillingshire was made up of the Borough of Richmond and five wapentakes of Gilling West, Gilling East, Hang West, Hang East and Hallikeld. After the Harrying of the North, the land became capital of the Duchy of Brittany's Honour of Richmond (first as a barony, then a county and later a dukedom).

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