We have a very limited amount of information at our disposal to answer this question, but I can provide a review of the evidence, covering the encounters with Stonehenge of writers of every period, from the Romans to the Hanoverians, by adapting the information I summarised in two earlier posts:

Roman era

No certain Roman-era reference to Stonehenge survives.

Antiquarians have sometimes claimed to see a reference to the site in the works of the Sicilian Greek writer Diodorus Siculus, who wrote in the first century BC – before the arrival of the Romans, but at a time when Britain was nonetheless part of Europe's Iron Age trading network, not least thanks to its exports of Cornish tin. Diodorus draws on a lost account by one Hecataeus of Abdera dating back a further 300+ years to the 4th century BC, and perhaps on others, to note that the "Hyperboreans," in their northern island, which may have been adjacent to Gaul, worshipped Apollo in a temple there. What excited the antiquarians was the description of the temple; Diodorus described it as "spherical," but some translators hazarded "circular" as a translation instead, seeing in this a reference to Stonehenge.

u/Tiako excerpted Diodorus's passage here a couple of years ago as follows:

Now for our part, since we have seen fit to make mention of the regions of Asia which lie to the north, we feel that it will not be foreign to our purpose to discuss the legendary accounts of the Hyperboreans. Of those who have written about the ancient myths, Hecataeus and certain others say that in the regions beyond the land of the Celts there lies in the ocean an island no smaller than Sicily. This island, the account continues, is situated in the north and is inhabited by the Hyperboreans, who are called by that name because their home is beyond the point whence the north wind (Boreas) blows; and the island is both fertile and productive of every crop, and since it has an unusually temperate climate it produces two harvests each year. Moreover, the following legend is told concerning it: Leto was born on this island, and for that reason Apollo is honoured among them above all other gods; and the inhabitants are looked upon as priests of Apollo, after a manner, since daily they praise this god continuously in song and honour him exceedingly. And there is also on the island both a magnificent sacred precinct of Apollo and a notable temple which is adorned with many votive offerings and is spherical in shape. Furthermore, a city is there which is sacred to this god, and the majority of its inhabitants are players on the cithara; and these continually play on this instrument in the temple and sing hymns of praise to the god, glorifying his deeds.

It's very much a matter of speculation as to whether Diodorus and his predecessors were onto something here, and were muddling accounts of a circular temple and turning them into one that was spherical, or whether the passage refers to some other site entirely. But it's well worth pointing out that, even if the original report was of a circular temple, it might refer to a number of sites other than Stonehenge.

Anyway, for the Roman period, that's all we've got.

Saxon era

The word "Stonehenge" is a corruption of the Saxon Stanenges, "hanging stones". It's usually supposed the name was given to the site because the trilithons at its centre reminded people of gallows. Some support for that supposition comes from the discovery of the victim of a Saxon-era execution (an articulated skeleton known to archaeologists as "burial 4.10.4"), whose remains were found in 1922, inhumed in the north-east ditch that surrounds the monument. These remains were long thought lost, but when rediscovered in 1999 they were carbon-dated to c.600-690. The victim, a male of 5 feet 4 inches (1.65m), who may have been either Saxon or a Briton, and was aged 28-32, had been decapitated with a single well-aimed blow from an axe or sword. Pitts et al observe that several known Saxon execution sites are associated with Neolithic monuments such as long barrows. Hence we have some evidence that for the early Saxons, Stonehenge may have been an execution and funerary site. Also worth noting, Pitts says, is that this burial is "the oldest indication we have that Stonehenge had a significance in recent centuries."

u/alriclofgar provided some important extra information on Saxon activities at the henge in one of the earlier threads I mentioned above, and you can read his contribution here.

Norman period

The earliest definite surviving reference to the stones can be found in Henry of Huntingdon’s Historia Anglorum, dating to c.1130. In this work, Henry lists Stanenges (a word that etymologists inform us is derived from the Old English stan(stone) and hengen, hanging – perhaps from the resemblance of the trilithons to gallows) as the second of the four wonders of England. The first of these wonders is the great cave of Wookey Hole in the Mendips; the other two are natural phenomena, one being a wind that emerges from certain caves in the Peak District and the other an atmospheric phenomena of some sort. So by the Norman period at least, Stonehenge was recognised as a remarkable, and in many ways unparalleled, achievement.

It's also interesting to note that Henry describes the site straightforwardly, without the sort of accretion of myth we might expect:

"The second marvel is at Stonehenge, where stones of amazing bigness are raised in the manner of gateways, so that gateways appear erected over gateways; nor can any one find out by what contrivance stones so great have been raised to such a height, or for what reason they have been erected in that place."

For the first stages in the construction of a legendary Stonehenge, we need to turn to that well-known myth-maker Geoffrey of Monmouth, whose 12th century Historia Regum Britanniae discusses the site as a monument to the ancient British history he was at such pains to construct.

For Geoffrey, who claimed to base his work on a probably non-existent old Welsh book, Stonehenge was a memorial to British soldiers killed by Saxon invaders led by Hengist in the fifth century AD, and later the burial site of Constantine, Arthur's successor as King of the Britons, and two of Constantine's sons: Uther and Aurelius Ambrosius.

"At Amesbury," Geoffrey Grigson summarises Monmouth's work,

the Saxon Hengist traitorously murdered an assembly of British notables. Later, when he had defeated the Saxons, the British king Aurelius Ambrosius determined to surround these noble dead with a monument. Merlin advised him to fetch from Mount Killaraus in Ireland a marvellous mystic and healing structure of stones which set, up again around the dead, would stand for ever. The stones were fetched, Merlin using his magic in dismantling them and re-erecting them. Within this Stanheng, this chorea gigantum [Giants’ Dance], Aurelius was buried, as well as Uther and Constantine.

Thanks to Geoffrey, the idea that Stonehenge was a tomb became quite well accepted in the medieval period.

From 1130-1530

Stonehenge again goes largely unrecorded in this period. The historian and Tudor propagandist Polydore Vergil mentions it, but only to repeat Monmouth's account.

Mid to late Tudor period

The first known image of Stonehenge was executed probably by Joris Hoefnagel in 1568 or 1569. The original is lost, but several versions of it exist, including a print by "R.F." and a watercolour by Lucas de Heere. It's notable for its inaccuracy, showing the stones as "curvaceous as a Modigliani nude" (Burl) and focussing, as do so many later descriptions, on the sarsens rather than the less well preserved bluestone circle.

The topographer William Camden mentions the site in his Britannia (1588), though without devoting the sort of attention we might expect from our more modern perspective. He focused on the monuments; physicality, calling it "a huge and monstrous piece of work," made of "certain mighty and unwrought stones." He added that some thought the stones themselves were artificial, not things that had been quarried and carved, being stuck together with "some glewie and unctuous matter".

Good stuff..thanks.