The medieval core of Richard's Castle is on a fairly confined site atop a spur between two valleys (neither carrying a river). The castle itself is believed to be one of the handful of Norman fortifications erected in England before the Conquest, in this case by Richard Fitz-Scrobe, who also held manors in Worcestershire and Shropshire, his barony often being known as the Honour of Burford. He was succeeded by his son, Osbern Fitz-Richard, who was the holder in 1086, when the castle is referred to by the name Auretone. A village is evidenced at the same period and a church was in existence by the twelfth century. In the early twelfth century the family became linked by marriage to the Says of Clun and lordship of Richard's Castle eventually passed, for reasons that are not entirely clear, into Say hands, bypassing male heirs of the Fitz-Richard line. By the late 1190s Margaret Say had, as a minor, become the heir to the barony of Burford and she took it in marriage to several husbands in succession, the second of whom (married ca. 1211) was Robert de Mortimer, of a junior branch of that family (more closely related to the Norfolk than the Wigmore line) whose patrimonial land was in Essex. However, a male member of the Say family contested Margaret's inheritance and the lawsuit was still going on in 1215.
Foundation of a town presumably coincided with the licence acquired in 1216 by Robert de Mortimer (d.1219) for a Thursday market and six-day fair in August, around the feast of St. Bartholomew, to whom the local church was dedicated. By remaining faithful to King John during the baronial revolt, even though the Norfolk Mortimers had joined the rebels, Robert had won royal gratitude that expressed itself, in the last months of John's life through the licence grant, among other favours. The licence does not necessarily represent initiation of a market at Richard's Castle, but more likely the desire of Robert (who did not associate his wife in the licence) to take advantage of the good-will of the king to make more secure his tenure of the market, and indeed of the manor itself, to which he had no hereditary claim. Robert also pursued a market licence for Stapleton, another component of the Burford barony, but was unable to complete negotiations for one before his death.
Robert de Mortimer died at around the time Margaret bore him a son and heir, Hugh; Margaret soon remarried William de Stutevill, so before Hugh de Mortimer could come into his inheritance, after coming into his majority, he had to wait for the death of William in 1259. As William only held by the custom known as 'courtesy of England' which suggests he had at least one child by Margaret and Hugh was constantly trying to reclaim his inheritance, William is unlikely to have invested much in maintaining or developing the castle or borough; in 1242, following Margaret's death, Hugh sued William for waste (failing to maintain the real assets of the barony), though this may just have been a ploy, for he dropped his suit upon Stutevill conceding him some of the lands of the barony . Hugh ought to have been more attentive to it; his interest in developing the fiscal potential of his estates is indicated by his acquisition, in 1266, of licence for a market and fair at Burford, in association with a borough foundation approved by the king. The timing of this licence and borough charter suggest them a reward for Hugh's adherence to the king during the struggle against the Montfortians.
In 1301 Robert's great-grandson, another Hugh de Mortimer, lord of Burford, conceded his burgesses of Richard's Castle, along with tenants of other districts, various rights in consideration of services they had performed during the Welsh war of the 1290s; their aid had probably been particularly valuable because Hugh had been a minor until 1296 and so not in full control of his own destiny. In 1304, on Hugh's death, there were said to be 103 burgages in the town, though we do not know if they were all occupied. Hugh also held a castle-town in the commote of Bleddfa, Radnorshire, though this had been, since the twelfth century, of the Burford barony though isolated after the Mortimers of Wigmore acquired the Honour of Radnor and it is unknown who was the founder, or what condition it was in by the time of Hugh's lordship, for the castle seems to have been abandoned rather than rebuilt after damage suffered in 1262 when captured by Llewellyn ap Gruffydd. Hugh was succeeded by two daughters, the elder of whom, Joan, had Richard's Castle as part of her share of the inheritance, while the other daughter had Burford and Stapleton Castle. Richard's Castle later came into the family of Joan's second husband, Sir Richard Talbot, upon the death (1375) of whose grandson, John Talbot, we hear again of the fair at Richard's Castle, still generating toll revenues. But no further market licences are evidenced, and the estates were further divided among female heirs after 1375.
The castle on the west side of the site was the product of progressive development in the twelfth and thirteenth centuries. The church, whose oldest fabric dates to the twelfth century, stood immediately east of the castle and the settlement ranged around that, to judge from the surrounding circuit of a ditch and rampart defence connecting to the north and south sides of the castle's outer earthworks. Finds of twelfth and early thirteenth century pottery are associated with the rampart. East of the churchyard was a triangular area with roads converging on either end; it seems likely this was the marketplace. Tenement plots were around it; the number of burgages in 1304 suggests quite intensive building within the town's defensive circuit, given that much of that area was consumed by churchyard and marketplace. However, the passage of time has obliterated much evidence of the medieval layout of the town, the modern village having refocused away from its medieval counterpart. Roads from the north and east passed through the town defences to converge on the marketplace; that parts of these are holloways points to their antiquity.
Several miles to the west of Richard's Castle was the longer-established castle and borough of Wigmore, while Ludlow to the north was even closer. Faced with this competition neither the fortification nor the market town at Richard's Castle in a location somewhat remote from significant overland or river routes were likely to maintain any importance. Although the castle continued to be strengthened through the thirteenth century, by the sixteenth it was becoming ruinous and the town (if it still remained one) depopulated, partly because residents were relocating away from the castle. The medieval town site was given over to farm buildings none appearing to embody any medieval fabric and fields in the post-medieval period and continues in that use today. We can conclude that Richard's Castle had ceased to have any urban function by the close of the Middle Ages and was superseded by a village on another site.