Wootton lay within the interior of Wiltshire, in an area with relatively little competition initially, although in the longer-term the development of Swindon, just a few miles away, must have proved detrimental. Situated atop a ridge, along which its High Street would run, Wootton lacked access to any watercourse significant enough to foster much industry, although water was available from springs and wells along the ridge. In documents from seventh to mid-eleventh centuries we hear of an estate at Wootton belonging to Malmesbury Abbey; yet Domesday Book shows it under a different holder, and it later became part of the Honour of Wallingford, whose lord was Prince John from 1189 and his descendants, the earls of Cornwall, for much of the reign of Henry III. In 1086 Wootton had the appearance of a small village without even its own church.
By 1200 the manor of Wootton was held, of the honour, by Alan Basset, a man then reaching his prime, who was in that year in the process of solidifying his hold on the advowson to the church; an existing manorial residence was probably situated just south-east of the village. The large Basset family, Norman in origin, had a history of service to the monarchy, particularly in judicial roles, having been "raised from the dust", as the chronicler Orderic somewhat unjustly put it, by Henry I. Alan (ca. 1175 -1232/33) was a younger son of Thomas Basset, though named for his mother Alice's father, Alan Reginald de Dunstanvill. Thomas, whose services in wartime had brought him a grant of the manor of Headington, Oxfordshire, subsequently served as sheriff of that county (1163-64), an itinerant justice, and a baron of the Exchequer; in 1178/79 Thomas, who was already sub-tenant of a number of fees of the Honour of Wallingford, farmed the honour from the Crown and his son Gilbert did so afterwards. Thomas' own uncle or grandfather had also been a sheriff and a chief justice to Henry I. While his older brothers were lords of Headington, the family base, Alan served first Richard I, who rewarded him with some lands, then John, who in 1203 granted him part of the manor of Wycombe (Bucks.) and subsequently recognized it as a barony. The manor incorporated a large vill where burgage tenure had apparently been implemented by the 1180s and which was sometimes known as Chipping Wycombe; this lay on a London-Oxford route and beside the River Wye. Alan was often in close attendance on John's court and in Magna Carta was identified as one of the king's counsellors in the negotiations with the barons. In his later years Alan supported the young Henry III.
(High) Wycombe became the head of his estates, and Alan is recorded as holder of its market in 1222, perhaps another concession by John to reward a loyal servant, though alternatively Wycombe may have had an informal market before Alan became the manorial lord, serving as a redistribution point for grain of the region, much ending up as part of London's food supply. But Alan was in conflict with his tenants there, who claimed to have burgess privileges by grant of Henry II such as a merchant guild with trade monopoly and with the abbess of Godstow, who also had seigneurial rights in Wycombe. One of the abbess' complaints was that Alan was exacting a fee of 4d. from houses facing onto the High Street, some of whose tenants were the abbess' men; this payment might indicate a burgage rent though other evidence ties it to the market, suggesting perhaps a form of stallage or a licence fee to trade in the market. Furthermore, post-medieval cartographic evidence suggesting the borough to be a relatively small area around the High Street, surrounded mainly by agricultural land, we can posit that the borough originated as a marketplace settlement. Perhaps encouraged by the abbess having made complaint to the king, Wycombe's burgesses complained that Alan refused to recognize their guild though they could not produce their royal charter, alleging it had been destroyed with the parish church during the Anarchy (a castle at Wycombe, overlooking church and borough, being belived to have then undergone a siege) was trying to impose his control over the town and its trade purely for his own profit. Having already come to terms with the abbess, and the burgesses' protracted lawsuit having been upheld in court, in 1226 Alan settled disputes with them by recognizing their guild and by granting the borough and its financial institutions to the burgesses, on a fee farm basis. [William Stewart-Parker, "Alan Basset and the men of High Wycombe", Henry III Fine Rolls Project, 2009, https://finerollshenry3.org.uk/content/month/fm-12-2009.html; last visited 9 January 2019; D. Green and R. Beckley, High Wycombe: Buckinghamshire Historic Towns Assessment Report, Buckinghamshire County Council, 2011.]
Five of the fees with which Alan ended up were part of the Honour of Wallingford; of these Wootton Bassett and Broad Town, also in Wiltshire, were held as the inheritance of his wife, Alina de Gai, daughter of a castellan of Cricklade who was himself a grandson of Henry I. When Henry III came to the throne, the trust the monarchy had in Alan saw him appointed sheriff of Rutland (1217-29) and, for part of 1219-20, sent on a diplomatic mission to France. Of his several children, by two or three wives, his son and heir Gilbert was married to a daughter of the Earl of Derby and, although briefly alienated from the king, after returning to favour became a close counsellor. Alan's second son Fulk became Bishop of London, while younger son Philip was the second husband of Ela Longespée, Countess of Salisbury (daughter of the founder of Lacock Abbey) and served as Justiciar of England 1261-63 (a period when Henry III had regained control of government from the barons).
Even before Alan's initiatives at Wootton and Wycombe, his family had been active in market development. One of his elder brothers, Gilbert, had as a young man been authorized, or so he claimed, by Henry II at some point during the last years of his reign, to establish a market in his town of Uxbridge (Middx.) with any pertinent customs. Gilbert's charter asserting this claim founded a borough, permitting anyone holding a one-acre property in the town exemption from market tolls in return for a payment of 2s. annually, while a tenant of half an acre was to pay 1s. for the same privilege; that these payments were burgage rents rather than trading licences is indicated by the charter specification that tenants were free to alienate (except in mortmain) the plots and the buildings they erected there, so long as the payment to the lord was preserved. The charter also seems to acknowledge that trading would go on, outside the market-day, in the houses of artisans. Much later evidence suggests there were around 80 burgage plots in the new town [On the Uxbridge situation, see G. Redford and T.H. Riches, The History of the Ancient Town and Borough of Uxbridge, Uxbridge, 1818, pp.17-42, and the VCH Middlesex, vol.4, p.74]. In 1194 Gilbert and his wife acquired a market licence for their manor of Stratford (Bucks.), and possibly founded a planned settlement there, which later amalgamated with one or two adjacent settlements belonging to different manors, to form the borough of Stony Stratford. The generation following Alan continued with like initiatives: his son Philip obtained a market licence for his manor of Kersey (Suff.) in 1252, and in 1262 licence for a second market and a fair for his manor of Upavon (Wilts.), neither of which, however, is known to have involved planting new towns.
After acquiring Wootton, Alan Basset proceeded to develop a wooded park near the manor, through enclosure, for which royal authorization was obtained in 1230; while the park was partly for hunting purposes, it may also have been intended to bring land into the demesne for cultivation and/or pasture. To the south-west of Wootton, atop a high point on the far side of a dip in the ridge where a brook cut through it, Alan's son Gilbert, immediately upon succeeding, built at Vastern a new family residence, large and fortified, though that at Wootton was not abandoned; developing and maintaining the extensive new manorial complex and its enclosure provided employment for workmen over the next couple of centuries, some of whom were doubtless Wootton residents, although some services would have been obtained through the obligations of villein tenants. Gilbert's successor, his brother Philip, created a second park before 1267, when it was said to lie beneath the town of Wootton; within a couple of years we hear of the existence of a manor of Vastern, though in the late fifteenth century it was merged with that of Wootton. At the latter period legal documents start to differentiate the manor and the town; although the name Wootton Bassett did not become fixed until the sixteenth century, it is occasionally found during the Bassets' tenure. Philip Basset founded a hospital-priory within the town in 1266, just north of the church (which is first mentioned in 1200 and none of its surviving fabric is of earlier date); the hospital was not well-endowed and was dissolved in the early fifteenth century, no remains of it now being known or having been found through archaeology. Philip (d.1271) was succeeded by a daughter, whose son Hugh le Despenser succeeded upon her death in 1281. The emparked area continued to grow under Despenser and later manorial lords (who were mostly members of the royal family), partly by eating up fields belonging to Wootton. The large park inhibited the development of roads through much of the parish, although there was already a northeast-southwest route connecting Chippenham and Cricklade, part of which served as Wootton's High Street; and off this stretch another road headed south-east to Marlborough, though it is not clear whether this was in existence during the medieval period.
Wootton has not left much trace in surviving medieval records. Alan Basset acquired a licence for a Tuesday market in January 1219. The inquisition post mortem on Philip Basset (1271) estimated the annual value of market tolls as 50s., while the manorial court was considered to earn the same amount, suggesting these were rough assessments, although a respectable one compared to tolls from some other small Wiltshire towns. A similar inquisition at the death of Philip's daughter, Alina, in 1281 lumps together the toll from market and fairs, worth 30s. per annum. No fair grant is known, but with the value so reduced after only ten years, we must imagine any fair at Wootton as of brief duration and not a major attraction in the region; it would be risky to conclude, based on these two approximate figures, that Wootton's market was in decline; however, Swindon's market had been in operation since about 1260 and this competition which was bothersome to Marlborough, farther afield would likely have detracted from the amount of business seen at Wootton. The inquisition post mortem on a later lord, in 1334, makes no mention of market or fairs, but is the first to mention explicitly both burgesses and burgages, which were producing an income of £7 3s.3d in rents, although such were probably subsumed under the classification of 'free tenants' in earlier inquisitions.
We have an earlier reference to Wootton's burgesses in 1236, in the context of royal instructions to the sheriffs of Wiltshire and Buckinghamshire to permit Gilbert Basset to levy a tallage on his burgesses at Wootton and Wycombe. As noted above, Alan Basset, as lord of the manor of Bassetbury, another component of the Honour of Wallingford and the probable focus for urban development at Wycombe, had turned the borough and some of its revenue sources over to its residents, but the degree of autonomy he conceded did not prevent him from imposing a tax on them whenever the king tallaged his demesne.
The High Street of Wootton Bassett long, straight, and wide flanked by burgage-type plots, has the look of a small planned town; it extended to just beyond the church at the south-west end of the street. The location of the earlier village is uncertain. We might expect it to be between the church and the original manor-house, yet the through-road interposes between those two; besides, we do not know a church existed when the village came into being. So a village near the manor-house is more probable, although the latter's site is itself uncertain. If, on the other hand, the village surrounded the church, some of it would have had to be demolished to make room for the planned town. The purpose of such a foundation was likely partly to supply goods and services to the estate the Bassets were developing at Vastern, and partly to enhance manorial revenues. There was little more to the town than its axial street, besides a couple of side-lanes which did not run far; it did not undergo much, if any, expansion during the Middle Ages, nor was there even encroachment on the marketplace a reflection of the market's mediocre performance. If, as the author of the Extensive Urban Survey report [p.11] suggests, the shape of the churchyard makes it look as if an element of the town plan, and the church was only built around 1200, then we would have to consider the town as under development, and an informal market operating, some two decades prior to the issue of the market licence.
Although perhaps achieving modest success in its early years, in terms of commercial activity, Wootton Bassett never became more than a small market town, its economy remaining based on agriculture as far as we can tell; there is no evidence of any significant cloth-making industry having developed during the medieval period. Its market lacked any advantages that would have enabled it to compete as better-placed markets emerged in the region. It may also be that the Basset family was more successful at suppressing local ambition and initiative at Wootton than was the case at High Wycombe; local administration was through the lord's leet court, which dealt with some market-related offences, until about the early fifteenth century, when we start to hear of mayors, the earliest having the surname Woolmonger. Wootton was not instructed to send representatives to parliament until 1446. Shops there are heard of in the late fifteenth century. Wootton's urban development seems generally slow and unable to lift it to a position that would give it the prosperity several other Wiltshire towns managed to build; during the Middle Ages it was perhaps not much more than a manorial appendage.