Stapleton was situated on the slope of the valley of the River Lugg, on the north side of the river, which here marked the county boundary. It was originally within the Shropshire manor of Stanage, waste at the time of Domesday. It has generally been thought that its name, not documented until 1207, referred to a settlement by or on a steep slope. However, as this is not a good description of its actual topography, there has been speculation that the prefix in the name might derive from a term used for a place where produce of the vicinity was bought and sold (in essence, a market); support for this theory comes from the equivalence of names Market Lavington and Staple Lavington. A castle, first mentioned 1207 but thought to have been built in the 1140s, became the centre of the Marcher lordship of Stapleton and continued in use throughout the medieval period; it was erected on the summit of a hill

In 1197 the underage Margaret Say, successor to the lordship of Burford – of which Richard's Castle was the caput and Stapleton a component – was married to Hugh Ferrars, who although also young lived only a few years, his patrimonial estates passing to his sister Isabella, wife of Roger Mortimer of Wigmore. An interval followed in which Margaret became the ward of Thomas de Galwey, Earl of Athol, apparently with the intention of marriage; he thereby had control of Richard's Castle and Stapleton Castle, but failed to achieve his marital ambition before he fell into royal disfavour, and worsened the situation through a raid on York. In 1211, only just reaching child-bearing age, Margaret took a second husband, Robert de Mortimer, and their son, born around the same time that Robert died, inherited the barony – though only some forty years after his birth, following the death of Margaret's third husband, William de Stuteville, who held the baronial estates by right of his late wife. One or other of the last two husbands (accounts differ as to which) was pursuing a market licence around 1216, though a grant was not forthcoming until 1223 and even then was provisional upon confirmation once Henry III had come of age. It seems likely that Margaret de Say was the driving force behind this initiative, for if these dates are correct, then it must have been her Mortimer husband who was persuaded to act on it, for he did not die until 1219, but Stutevill presumably saw it through to completion, though there is no indication of confirmation of the grant after King Henry emerged from his minority in 1227. It may well have been around the time that a market licence was being sought that a town was established at Stapleton.

The inquisition post mortem on Hugh de Mortimer, baron Burford, in 1304 gives us our first reference to burgesses , there being 34 in Stapleton itself and its hamlet of Froggestrete, which lay at the south end of the town, on the north side of the ford across the Lugg. Hugh left only two daughters, so that the barony was divided; in that same year Stapleton and Burford passed, by marriage to the younger heiress, Margaret, into the hands of Geoffrey de Cornubia, whose surname records his descent (by illegitimate line) from King John's son, the Earl of Cornwall; Margaret was not yet of child-bearing age, Geoffrey about 15. In 1334 Geoffrey, acquired royal grant of a Friday market – whether an additional market day or (more probably) just renewal of the earlier grant is unknown – and of fairs in July and November. The purpose of the licence was probably to bring Stapleton more securely into the inheritance of his children, rather than being an indication that the town's commerce was either growing or needed revitalizing. Already in 1316 he had made similar provision regarding the manor, granting it to his mother, who granted it back to him and his heirs, and this he followed up by obtaining a royal grant of free warren there. Taking the same precaution with the market may have been an indicator of declining health; at any rate, Geoffrey died the year following renewal of the licence, but Stapleton was passed down his male line into the post-medieval period, apparently properly maintained as a residence.

The hilltop castle rose above the Lugg valley; the town was situated lower down the slope, immediately to the south and east of the castle, though its depopulation from the fourteenth century onwards has meant that property boundaries have not survived well. This location put Stapleton in competition with the market town of Presteigne, to the south-west on the other side of the river and thus technically in the Radnor region of Wales, although later integrated into Herefordshire. Presteigne was a village with its own church by the Late Saxon period and had, after the Conquest, been part of the barony of Burford, whose lords built a castle there, on the opposite side of the settlement to the church, which was situated close to a crossing-point of the Lugg and whose fabric incorporates some early Norman and, more conjecturally, Anglo-Saxon remnants [Andrew, Medieval Small Towns in the Central Welsh Marches: An Analysis of their Development, Durham University MA thesis, 2017, p.73-75]. But the castle had been seized by Roger de Port, lord of Kington, in 1143, and this may have been why the castle at Stapleton had been put up, as a base from which to try to retake Presteigne, an effort that proved unsuccessful. Stapleton was within Presteigne parish and had no church of its own. Presteigne developed into a town around the same time as Stapleton, or a little later, there being references to burgages in thirteenth and fourteenth centuries, and to a High Street and a Broad Street, the latter leading from its junction with the former – an intersection around which are clustered some of the oldest surviving domestic buildings – down to the river-crossing, while the north-western arm of the High Street curves around the castle bailey (in the opposite direction it becomes the road to Hereford).

Licence for a market and fair at Presteigne was obtained in 1225 by William Fitz-Warin, although this was reversed three years later, and the Exchequer instructed not to pursue collection of the licence fee of 5 marks; this was on the grounds Fitz-Warin was no longer in possession of the manor – if indeed he ever was, for there may have been a confusion between William Fitz-Warin, the castellan of Hereford, and William de Fraxino, whose father was also named Warin, seen quitclaiming the advowson of Presteigne's church to Wigmore Abbey in 1236 [on this see W.H. Howse, "Early grant of a weekly market to Presteigne," Radnorshire Society Transactions, vol.26 (1956), pp.43-45]. Possibly William de Fraxino was, in 1238, charged the licence fee, though we have no record of that. Certainly a market and two fairs – one on the same festival as that of the 1225 licence – were held at Presteigne by Edmund de Mortimer of Wigmore at his death in 1304, though the market day differed from that of the 1225 licence; Edmund also held the market towns of Wigmore, Pembridge, New Radnor, and Cleobury Mortimer in that region. The Mortimers acquired Presteigne by marriage to a Braose widow ca. 1230, and so it may have been this pending transfer that prompted Fitz-Warin to seek revocation of his fiscal obligation for a market from which he could not now profit, while the more powerful Mortimers felt no compulsion to formalize their ownership by purchasing a licence. Presteigne may not have shown much economic promise at that period, for tax records from 1293 show only 17 Presteigne contributors, even though a rent roll of 1300, albeit fragmentary, identifies more than 70 residents, suggesting that most of the latter may not have been prosperous enough to be taxed.

That Presteigne's market was able to operate so close to that at Stapleton is indicated by the manorial court roll of 1339/40, which includes sometimes heavy fines imposed on men who had tried to evade paying toll; yet apart from tailors there are surprisingly few occupational designations or surnames evidenced in surviving Presteigne records that would suggest the presence of much industry, although a tannery is suggested by Tan House in Broad Street (tree-ring dated to 1436), close to the Lugg bridge, while brewing is documented through the number of male and female residents regularly fined for breaking the assize or for over-diluting. Neither town fared well in the face of the adversities of the fourteenth and early fifteenth centuries; Stapleton was said, perhaps with some exaggeration, to have been razed to the ground by a fire in 1335, its bailiff drowned in the Lugg, perhaps in seeking to escape the conflagration [Calendar of Inquisitions Post Mortem, vol.10, file 332], though this type of disaster was more easily surmountable than the loss of population to plague. By the close of the Middle Ages Stapleton had been reduced to a village without a market, and Presteigne's market was also discontinued for a time, though the Bishop of St. David's (himself a native of the place) headed a redevelopment initiative at Presteigne that included grant of a market charter in 1482, and this revived market was prospering by Leland's time. Today Presteigne still thrives as a small town, whereas Stapleton is barely a village, with only a couple of dozen residents, and nothing to suggest to the onlooker its brief span as a market town.

Where lay Stapleton's marketplace is unknown, but the town was served by only one each of a north-south road (along which ran a brook) and east-west road – the latter linking to Presteigne via a river crossing – and their crossroads, just east of the castle, is a likely location; apart from the castle ruins, the only surviving medieval building (early fourteenth century, but also ruinous) stands here. This possibility receives tentative support from the existence next to the posited marketplace – in one corner of the crossroads – of a building once known as St. Mary's house, which might, the EUS report authors suggest [p.3], mark the site of a chapel that would have been desirable in a community without its own church. That Stapleton was not especially well connected, in terms of the road system, is suggested by the fact that the only arm of the crossroads still in use today is that leading to Presteigne, and even that has been superseded by a second road from the east, perhaps established after the decline of Stapleton town and castle, for it circumvents the castle and avoids the Stapleton marketplace in order to provide a quicker connection to the river crossing to Presteigne.