The manor is mentioned in Domesday, its name suggesting it may have been the administrative centre for a group of surrounding estates all of which had belonged to Edward the Confessor or King Harold. However, doubtless due to its location near the border (in fact it is on the Welsh side of Offa's Dyke), it was deserted by 1108 when Henry I granted it, among a group of manors, to a member of the de Port family as the Honour of Kington, a Marcher lordship which would have required establishing a castle-town there. The earliest mention of a castle is in 1186, when in need of repair. The site chosen for the typical grouping of castle, town and church was atop a small hill above the River Arrow, itself in the shadow of Hergest Ridge.
The church, whose dedication is to St. Mary, was constructed, or perhaps rebuilt, during the twelfth century; its tower, completed ca.1190, is not properly aligned to the rest of the church, indicating it had belonged to an older building, perhaps even pre-dating the castle. The proximity of church to castle suggests both may have been built within a defensive circuit [Tina Andrew, Medieval Small Towns in the Central Welsh Marches: An Analysis of their Development, Durham University MA thesis, 2017,, pp.90, 99]. As settlement later spread down towards the river, to focus around the High Street, the original town became known as Old Kington, and its burgages (like the castle) were gradually abandoned. These original and later foci for settlement Old Kington (Castle Hill area) and New Kington (focused on the junction of Bridge Street with the High Street, expanded, apparently in planned phases, down Bridge Street and up Church Street) were connected by Church Street. Burgage-type plots have survived or at least are most evident in New Kington.
A descendant of de Port lost possession after rebelling in 1173, so the Honour of Kington came into the king's hands, and the manors of Kington and Huntington were in 1203 granted to William III de Braose, who had some claim to the lands through his mother, daughter of an Earl of Hereford. There exists some confusion about the identities of the members of the de Port family who received and lost the Honour of Kington. The EUS report follows R. Kay in identifying the original grantee as Adam de Port and the rebel as Roger de Port. In 1121 the king confirmed Adam de Port's grant of land in Kington to the monks of Tiron [Regesta Regum Anglo- Normannorum 1066-1154, vol.2, p.165]; this Adam, referred to on one occasion as a baron of Herefordshire, was evidently in frequent attendance at court, occurring as witness to royal acts 1111-29, while the nature of several royal communications addressed to him suggests he was sheriff of Herefordshire for at least part of the period 1111-21. A man of this name is identified as a baron in 1086 and was a relative (perhaps brother) of Hugh de Port, sheriff of Hampshire in 1196 [ibid., vol.1, pp.59, 97]; but this Adam is unlikely to have been the same as the Herefordshire baron.
On the other hand, a document issued by Kington's present-day town council identifies the grantee and forfeiter as, respectively, Henry de Port and Adam de Port; Tina Andrew [op. cit., p.97] also adopts the latter identification. The Dictionary of National Biography, [original series, vol.46], has this Henry de Port (son of the above-mentioned Hugh) as lord of Basing, Hampshire, and sheriff of that county at some point in the early years of Henry I's reign; his grandson Adam is documented as holding twenty-four knight's fees in Herefordshire of the widow of the Earl of Hereford. Accused in 1172 of plotting against the king, he fled, was outlawed, and later joined a Scottish invasion repulsed at Alnwick; coming to terms with the king in 1180 he received back his patrimonial lands, but not those in Herefordshire. However, it may be that this Hampshire Adam de Port was a different individual from that of Herefordshire. Disentangling these individuals is beyond the scope of this study. Be all this as it may, no-one of the de Port surname is associated with any documented market or fair licences.
The Braose lords were non-resident and at some point in the next few decades transferred the manorial administration to Huntington, abandoning the cramped castle at Kington severely damaged, along with the old town, in an assault by King John in 1216 before 1230, having built a larger castle at Huntington (perhaps consequent to the damage to that of Kington). Yet the residents largely stayed put, and Huntington proved unable to supersede it as the commercial centre of the manor. Indeed, the same period saw the planned town of New Kington, or Kington in the Fields, laid out with burgages (29 of them are heard of in 1564, each with a sixpenny rent), in late twelfth or early thirteenth century, closer to the Arrow; again, the damage to Old Kington in 1216 may have prompted such renewal, once Reginald de Braose had been restored to royal favour. In 1267 we hear that New Kington was doing well, generating 64s.3d in rents for its lord, whereas the burgus of (Old) Kington generated only 22s. It seems likely that market activities would have been transferred into the new town; no record of a market grant exists, but Old Kington's market would not have required it and nor would one that was merely relocated within the same manor. The transfer of the focus of settlement onto lower-lying ground closer to the river would have provided more scope for industries that required water access.
Kington was thereafter able to maintain a role as the principal market in that part of Herefordshire, and was one of only nine market towns to survive in the county, despite reduced population following the Black Death, as far as the close of the Middle Ages. It benefited from its proximity to the agricultural lands of Radnorshire, from the wool trade, and from the fact that the town was situated on an important drovers' route crossing Hergest Ridge to connect central Wales with England this may explain why Kington, as a centre for trade in livestock, would come to have several fairs. It remains today one of Herefordshire's market towns, albeit the smallest, and still has a weekly livestock market.
The castle, of which little now remains, was in the north-west corner of the site, atop a knoll; just north of it ran Back Brook, which was evidently the northern boundary of the settlement and probably its initial water-source. The churchyard lay on a steep slope a little south of the castle. The location of the original settlement and its market are unknown, but presumably close to the castle and the church, or conceivably even within the castle bailey; little trace is today evident of any streets or burgage plot boundaries there. By contrast, burgage boundaries in New Kington are still discernible in the earliest Ordnance Survey map. The market of New Kington ranged along the roughly east-west High Street, perhaps with a particular focus at a widened west end, where Church Street, descending the slope south-eastwards from the castle and church, joined it to create a triangular-shaped junction, and where a public well was situated; at this junction stood a market cross, while another (marking the far end of the market area) was at the High Street/Bridge Street junction, both being replaced by market halls in the post-medieval period. Burgage plots of New Kington were laid out around the southern stretch of Church Street, the High Street, its continuation eastwards (Duke Street), and a further street (Bridge Street) at the mid-point of that east-west through-road, running south to a bridge across the Arrow (probably built as part of the planned town). Lesser streets and lanes running off either side of the High Street and Duke Street delineate rectangular areas of tenement plots, served by back lanes; this reinforces the impression of a planned town, although we cannot be certain at what date these areas were built up.