Ludgershall lies close to the Wiltshire/Hampshire border, with the (roughly contemporary) borough of Andover in the latter county a few miles to its east. To its north lay forest, and thereby hunting possibilities. It is on a north-west to south-east road connecting Marlborough and Devizes with Winchester (via Andover) which had acquired some importance by the early thirteenth century. The earliest mention of Ludgershall was in 1015. By 1086 the small village was held by Edward of Salisbury, sheriff of Wiltshire; Henry I had resumed possession of the manor by 1103 and it was probably in his reign that a rudimentary castle was built, perhaps utilizing Iron Age earthworks. It was refortified in1138 by John Fitz-Gilbert, marshal of the empress, in light of the civil war, and he retained possession until his death in 1165, after which William Fitz-Peter held it for a while. Manor and castle were back in Crown hands by1174; King John, a frequent visitor, carried out improvements to make it more serviceable as a hunting lodge and royal residence, for it had little strategic value, and Henry III went even further in that direction, while also strengthening the defensive elements. The presence of a residential castle used by the king appears the main reason why the village at Ludgershall developed into a town; periodic upgrades and repairs to the castle, as well as royal visits, must have boosted a local economy otherwise reliant on agricultural activities.
No market licence is recorded – another indicator of the early foundation of the town – though one is implied in 1255, when the town was one of several in the region fined by the king for some market offence apparently related to the assize of wine; it is referred to more explicitly in 1268. In 1348 the townsmen complained that expansion of the hunting-park around the castle had lost them some of their common land and blocked off some of the northern routes into the town, obstructing merchants and others who wished to do business at Ludgershall; in compensation the king abolished the market tolls there, as a trade incentive. In 1248 the king licensed a September fair, and one in July is mentioned in 1291; the former is not heard of again, though the latter is, and perhaps they were actually the same.
Efforts to reconstruct the medieval town layout from present-day topography have produced two somewhat different interpretations, showing the uncertainties entailed in this kind of work, in the absence of surviving documents and with only minor excavations in the town itself. In either case urbanisation probably took place at some point in the twelfth century; it is difficult to narrow down to precisely when, but clearly it was linked to the growth of the castle. In 1194 Ludgershall was treated as a borough for purposes of presentments to the eyre; this is not necessarily reliable evidence, and we do not hear of burgesses until 1306.
The authors of the Victoria County History envisaged a grid layout for a planned town, as follows. The castle was located north of the through-road, to which it was linked by a street known, by 1598, as the High Street; this, perhaps widened, became part of a small grid of streets that suggest expansion of the village to create a planned town between castle and road, which was diverted north so that it passed through the town. The marketplace was held in the High Street, and perhaps particularly a wider stretch approaching the junction with the road to Winchester. A church was built in the twelfth century just west of the street-grid; none is mentioned in Domesday, so the church may have been constructed as part of the planned town, though presumably after the streets were laid out and initial settlers were established. Parallel to the High Street, to its west, ran a street that passed the church (Church Street); these two streets were connected by a parallel pair of lanes, the more southerly of which was placed to run westwards to the churchyard, while an extension eastwards led to the residents' common. The northern boundary of the town was the diverted through-road, which ran westwards from the top of the High Street, beside the castle's southern earthworks. Typical burgage-type plots lie on either side of the High Street. Other burgages seem to lie along the through-road where it approaches the High Street from the south-east, and leaves the town from the north-west.
The Extensive Urban Survey author, on the other hand, relying on results from a detailed excavation of the castle site in the 1990s, presents a more complex picture. It envisages the area between the High Street and Church Street as one huge marketplace stretching between the through-road and the castle – which would have been extravagantly and inexplicably large in comparison to spaces provided in other Wiltshire towns – with planned tenement layout on the east, west and south sides and incorporating the churchyard. The only identifiable burgage plot groups, according to this interpretation, are on the east side of the High Street and south side of the through-road opposite the south end of the marketplace; plots north and south of the church are of different shape and size and might have been shops, workshops, or animal pens. Archaeologists uncovered evidence of a cemetery in the block north of the church, but were unable to assign a date – perhaps a feature of the Saxon village. This interpretation argues that in mid-fourteenth century there occurred a southwards expansion of the castle, to increase its park, consuming part of the northern half of the marketplace and the northern half of the burgages on the east side of the marketplace. Infill by what might have been rows of shops also ate up areas around the western and southern edges of the northern half of the marketplace. This postulated castle expansion would explain the complaint of the townsmen, mentioned above. Erection of a market cross at that period, along with creation of the rows of shops, might then be an effort to revitalize the compromised market. At the same time, burgage plots were established along the through-road, approaching the High Street, to compensate for plots lost to the castle expansion.
Apart from the changes effected according to the latter theory of development, Ludgershall did not grow much from its original urban nucleus; it was one of the smallest towns in Wiltshire. We should not, however, blame the mid-fourteenth century disruption to the marketplace for this, although it appears to have been at least a short-term problem for commerce, and possibly longer-term since the castle and its park impeded growth of the town somewhat; the main causes come a little later. Although it sent representatives to parliament (one of whom, attending several sessions in the reign of Richard II, is known to have been a merchant) on a number of occasions from 1295 to 1330, Ludgershall was rarely summoned again until the reign of Henry VI. Nor did it develop any known institutions of self-government, even though the townsmen had managed to commute feudal labour obligations on the demesne farm before 1233 when they began to hold the borough at farm. The town being administered by the castle bailiff, who had less interest in nurturing the town's welfare than the burgesses should have had; their failure to advance administratively doubtless contributed to the stagnation of local commerce.
Ludgershall may have fared adequately as a small market town, at least prior to the problems, local and national, of mid-fourteenth century, but there is no evidence it had any competitive advantages beyond its placement on a through-road, and its economy relied at least partly on business generated by the castle. The site was not crossed by any watercourses large enough to have supported the usual medieval industries. During the later Middle Ages the manor changed hands with some regularity and may have been neglected; the church underwent expansion and renovations into the fourteenth century, but it then received little attention until its tower collapsed in 1662. The castle too was neglected, with royal visits becoming increasingly rare; it had become ruinous by mid-sixteenth century. The town had lost, by the time of a devastating fire in 1679, any importance it may have initially acquired. It was an impoverished village thereafter.
