Located in the north-western corner of the county, within a few miles of Malmesbury, the earliest settlement at Sherston was around a church atop a spur of land formed by a branch of the Avon, where there was a crossing. The Roman Foss Way marked the parish boundary to the south-east; the most important through-road ran from Malmesbury into nearby Gloucestershire, but passed by, rather than through, the vill of Sherston. The earliest documentary reference to the place is in 896, though archaeology has shown the presence of light settlement in the vicinity in earlier centuries. The settlement was still a small one at the time of Domesday. The church, which seems to have originated as a minster on a royal estate possibly coterminous with the Denley Hundred, was rebuilt in the late twelfth century, but the development from village to town must have taken place around the time of the acquisition of a market licence in 1241.
The manorial lord and licence holder was Matthew Bezill. Bezill was one of a number of foreigners cultivated by Henry III as favoured servants within his household; he was from Touraine, but without property there and of relatively humble origins; he may have been introduced to the royal court by Bishop Peter des Roches, also from Touraine, when he headed the regency during part of Henry's minority [Michael Ray, "Three alien royal stewards in thirteenth-century England: The careers and legacy of Mathias Bezill, Imbert Pugeys and Peter de Champvent." Thirteenth Century England, vol.10 (2003), p.52.]. The bishop sought to overthrow the powerful Hubert de Burgh's grip on the minority administration. However, the first mention of Bezill is not until 1233. He served Henry in capacities such as military escort accompanying, at different times, his queen or his brother, the Earl of Cornwall, overseas into Gascony, the earl of Norfolk to the papal court on royal business, and the king of Navarre through Gascony after a meeting with Henry. From 1254 to at least 1261 he acted as steward of Queen Eleanor's household; he died in 1268. His fellow Savoyard, Imbert de Pugeys, rose to become steward of the king's household and one of his rewards was the grant of the manor of Bampton (Oxon.), which had a market since at least the eleventh century.
As one associated with the Touraine soldiery who had served King John, Matthew had been proscribed by Magna Carta, and stirred up further resentment during the regency of des Roches; he faced a general backlash of anti-alien sentiment in England. Even his surname worked against him for, although just possibly obtained from the French community of Bézelle, it seems rather to derive from a French verb meaning to steal or plunder (and survives in our term embezzle). Henry III's policy was to attempt to assimilate his alien servants into English society (as well as assure them incomes supplementing their salaries) by granting them land and wedding them to native heiresses over whose marriages he had control. Sherston manor was granted Bezill for life in 1240, in lieu of an annuity from a different manor, once of Hubert de Burgh, though the terms of the market licence the following year suggest Bezill's ambition was to make his tenure more permanent, something he appears to have achieved by 1253, although his heir also held only for life.
In the years that followed the grant of Sherston, Henry sought out a wife for Bezill; that the first few ladies he approached evidently declined may reflect the feeling against aliens. In 1246 Henry persuaded Beatrice, the widow of John de Bassingham, to take him; the property she brought to the marriage, though substantial, was only held in dower, so could benefit Matthew only while she lived. Although she bore him children and stood by him, after his death she reverted to the name Bassingham which, while perfectly acceptable for women of noble birth, suggests she had no great attachment to him. It was their sons, John and Matthias, both described as king's yeomen, who, a few weeks apart in 1272 obtained licences for market and fair for their father's manors at, respectively, West Alvington (Devon) and Radcot (Oxon.); John de Besill – who had aggrandized his ancestry by converting his surname (originally a pejorative nickname) into a locative form – may have attempted to found a town at West Alvington, for burgesses are heard of there in 1304.
The market licence had been granted not only to Matthew Bezill but to whomever held the manor after him. Local commerce seems to have done well enough, for in 1248 Bezill acquired a licence for a two-day fair in July, then another for September in 1252; His marriage is evidenced by the fact the fairs were granted to him and his heirs, also an indication that his tenure of the manor had become firmer. Around 1256, however, he complained that a market at Hawkesbury (Gloucs.), licensed 1252 by the abbot and monks of Pershore, was damaging his Sherston market, and a local jury endorsed the complaint [Michael Ray, Mathias Bezill, the Unpopular Alien?, http://www.finerollshenry3.org.uk/redist/pdf/fm-05-2012.pdf, p.5]; this conflict may provide the context for a change in market-day at Hawkesbury in 1253, from Monday to Saturday, and/or the change in market-day at Sherston, already noted. A grant in 1247 of free warren in Sherston, to Bezill and his heirs, points to his marriage having taken place by then – the age of his heir suggests 1246. In addition to land at Netley (Hants.), which Bezill had by 1242 re-granted in mortmain to the Cistercian abbey there, the king also gave him the manor of West Alvington, in Devon, though Sherston, as the more developed property, was worth more (estimated at £36 per annum).
During the baronial war Bezill remained loyal; as constable of Gloucester castle he held off a siege, and in 1262 as sheriff of Gloucestershire he arrested a member of the baronial party, which opposed his appointment as sheriff. The king had granted him land in that county at Didmarton. In September 1258 he had been sentenced to imprisonment (though probably paid a fine to avoid gaol) after an eyre had convicted him of disseisin in regard to some land in Sherston; whether politics or anti-alien feeling was a factor here is uncertain, but he accused the local jury of swearing a false oath and of the complainant being his villein, though the jurors declared him a free tenant – he was perhaps a townsman. Bezill's manorial land at Sherston, which was later ravaged by enemies of the king. Whether these events soured him on Sherston we cannot know; the surviving inquisition post mortem record from Wiltshire deals only with his manor of Woodhill, which had, or would, become the family home, while Sherston is not in evidence; in 1280 and again in 1281 his son John was said to have only a life tenancy in the manor.
Given Bezill's loyal service to, and patronage from, the king, it is not surprising to find that mounted on the walls of Sherston's church are head-shaped corbels thought to represent Henry III, Queen Eleanor, the Earl of Cornwall, Simon de Montfort, and Ela Countess of Salisbury (although the last is more likely to be Eleanor, sister of Henry and wife of Simon). Apart from Ela, these were all people Bezill had known personally for many years.
By the time of the poll tax of 1377 Sherston's population had grown to the point that it seems to have been bigger than Calne; yet it was not of such consequence that it generated much by way of documentary references. Its economy may already have been in decline when a fire in 1511 caused widespread destruction. This decline could have been due to competition from Malmesbury. Sherston shows signs only of modest expansion in the Late Middle Ages – and even this was not manifested through the usual encroachment on the marketplace. Neighbouring Easton Town, further north along the through-road (which connected only to surrounding villages), could represent either suburban spread or an existing hamlet. The market, whose day had already been changed from the original Tuesday to Friday, was no longer held after the devastating fire. Sherston remained nominally a borough until 1832, when its status was changed to that of village.
The Saxon village and church were at the north end of Sherston's through-road; the manorial enclosure appears to have been south-west of the village. The town was laid out south of the village and east of the manorial enclosure, along the road (now the High Street), with burgage plots on either side (though these have no documentary reference before 1393), terminating at Back Lane on one side and Back Street on the other. The marketplace was formed, as a long rectangular area, along the High Street; perhaps with a particular focus in the southern stretch of the street, where stood the Tolsey, mentioned in 1511 as one victim of the fire; this is likely to have been a medieval structure, perhaps dating back to the formation of the borough.
