Headington Hill: Introduction
The steep hill that leads up to Headington (together with Headington Hill Hall) has always been part of the parish of St Clement’s. Historically, therefore, no part of the hill itself was deemed to be in Headington: it merely led to Headington.
The name Headington Hill was, however, also used as the name of the isolated hamlet that straddled the top of the hill and was on the outskirts of the parish of St Andrew’s Church in Old Headington.
Later "Headington Hill" came to mean the Headington Road (from the summit of the hill to the Boundary Brook, which has been diverted underground across the road beside the White Horse pub), including the side-roads that ran immediately off it.
On 15 May 1802 the new Lord of the Manor of Headington, Henry Mayne Whorwood, inserted an advertisement in Jackson's Oxford Journal putting out to tender the contract for building a five-foot wall "from the new intended Road near the White House" (the new road, to be called Manor Road, is now Osler Road, and the White House was the old name of the Britannia) to Joe Pullen's tree. Much of this wall still survives today along the north side of the Headington Road.

The detached nature of the Headington Hill settlement is emphasized by the way it floats around in the censuses:
- 1841: South side in the Quarry census (no houses on north side of the road at this time)
- 1851: North side in Old Headington census; South side in Quarry census
- 1861 and 1871: North and South side both in the Old Headington census
- 1881: North side in New Headington census; south side in Old Headington census
- 1891: North side in Old Headington census; South side in New Headington census
- 1901 (following boundary change): North side in Old Headington census; South side (i.e. houses west of the Boundary Brook) not included in Headington.
In 1889 Oxford was extended as far east as the Boundary Brook, with the result that from the early 1890s "Headington Hill" is listed as if it were a street in the city section of Kelly’s Directory, rather than as a hamlet in the county section. It is also described as if it were an outlying part of St Clement’s, becoming associated with the hill itself; but this connection vanished in 1929 when the city boundary spread further east again to include the whole of Headington.
Note
Early directories sometimes loosely describe detached buildings at the the west end of Old Road (such as the Warneford Asylum) and at the west end of the London Road (such as the White Horse and Brookside) as being "Headington Hill".
In this subsection of the website, Headington Hill refers just to the hill itself and Headington Road (which naturally comes to a halt at the Boundary Brook, which from 1889 signalled that the traveller had reached Headington, and was now about to embark on the turnpike road to London. The old lanes behind the Headington Road are included here, but not Pullen’s Lane, which merits a section of its own.
