There are good views of the spires of Oxford from the hill, especially from the top of South Park.

Between 1644 and 1646, Headington Hill was used by the Parliamentarian forces while besieging Oxford during the First English Civil War.

Headington Hill is the home of the Oxford Spanish Civil War memorial which is dedicated to local residents who travelled to Spain to join the International Brigades to fight against fascist forces backed by Hitler and Mussolini during the Spanish Civil War 1936-1939.

[1] Most of the volunteers were communist activists, and many had links to Britain's Jewish communities.

Oxford was a hub for anti-fascist activism, homes within the county housed hundreds of Basque refugee children and various physical fights between anti-fascist activists and the Oxford University Fascist Association.