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Stone Age: Long prior to this, the site was occupied during the Upper Palaeolithic. There is evidence of an open settlement of the Creswellian culture on the hill in the middle of the headland dating to around 10,500 BC. At the time, this hill would have overlooked a large river valley that was to become the English Channel. Later, once the sea had inundated the surrounding valley, Mesolithic hunter gatherers exploited the site and Neolithic stone tools have been found but it was not until the Bronze Age that visible traces of the site's occupation are apparent.

Bronze Age: Eleven Bronze Age round barrows sit on the promontory with two more a little further inland. Numerous finds including Early Bronze Age axes, along with Amber and gold jewellery were recovered from these monuments. Pottery found nearby to the barrows also indicates visitation during 1700-1400BC. In around 700 BC, a small settlement to the very north of the headland was established; also around this time, the headland was cut off from the mainland by the construction of two banks and ditches. These earthworks turned Hengistbury Head into a fortified settlement area which seems to have grown over succeeding centuries until it became an important port.

The barrows at the site were first excavated by J. P. Bushe-Fox between 1911 and 1912 and then by Harold St George Gray in the years following the First World War. Most of our knowledge of the site comes from Barry Cunliffe's work there between 1979 and 1984.

Iron Age: One side of the Head is defended by large earthworks, called the "double dykes", similar to those found at Maiden Castle. These date to approximately 700 BC Due to the high concentration of iron ore in the area, this location became a significant trading port, trading worked metal–iron, silver, and bronze–with the Continent in return for wine, tools, and pottery. Many coins have been found from this period (making it one of the few areas in pre-Roman Britain to use coins). Interestingly, some of them were fake–worthless cores dipped in silver.

Roman occupation: Under the Romans, Hengistbury Head was initially left alone, possibly as a result of its distance from Roman centres of power. However, as Roman rule expanded, trade was moved away from the Head to other Roman ports. Consequently, the region saw a decline in prosperity, and indeed, by about the time the Romans left (c.410 AD), the area was abandoned.

Medieval use: The area was not substantially reoccupied until Alfred the Great decided to rebuild the harbour as a defence against raiders. He built the town that later became Christchurch, on the north side of the harbour. Access to Salisbury up the River Avon made this a more strategic place. The Head may have been used for harbour defense at this time.

Nineteenth century: From 1848 to 1872, the Hengistbury Mining Company, formed by a local merchant, Mr. Holloway, extracted ironstone boulders. These form the base of Hengistbury Head, and the removal of a substantial quantity has weakened the headland. The quarry resulted in a loss of about a third of the Head, mainly by erosion since the quarry closed. The silt being washed down also threatened the ecology of the saltmarsh below. This has been reduced by building a dam, in 1976, to create a pool. Mr. Holloway brought coal from Southampton, and took the ironstone as ballast for the return journey.

Ghost hauntings