Ruyton of the Eleven Towns is on sloping ground on the western side of the River Perry. In Domesday it was simply known as Ruyton, and Eyton has it as Ruyton iuxta Baschurch, though it is not clear that name was ever applied to it during the Middle Ages. The character of Ruyton in Domesday is purely rural, it being waste before the Conquest, but re-development was initiated by its post-Conquest Norman holder; fisheries associated, probably in the river, were let to some of the residents, and a mill was built there. Ruyton acquired its unusual name, written with the Roman numerals, at some point in the twelfth century, when the lordship was expanded and Ruyton became the head manor for eleven local townships (small clusters of settlement), including Ruyton itself. It was at one time part of Baschurch Hundred, but later transferred to Oswestry Hundred (though remaining part of Baschurch parish), which Eyton [vol.10, p.112] suspected was consequent to the Fitz-Alan family coming into possession of Ruyton manor; William I Fitz-Alan enfeoffed John I le Strange in the manor and he donated to Haughmond Abbey (founded by William near Shrewsbury) a mill, while later members of the Le Strange family gave it a second mill, the advowson of Ruyton's church, and property to serve as its glebe.

Ruyton's promotion to a head manor, or caput, was probably associated with the construction there of a castle before mid-twelfth century; this was destroyed by a Welsh attack in 1212. The church, dedicated to St. John the Baptist, originated as the castle's chapel. Not long after coming into his inheritance(1306), Edmund Fitz-Alan, Earl of Arundel, bought back Ruyton manor from the Lestranges, clearly with the purpose of establishing a market town there, and presumably because he could see the potential in fostering an existing volume of commerce passing between Shrewsbury and Oswestry. He rebuilt the castle, and allocated an area, just west of the castle and manorial settlement, for a borough; planning and layout were evidently effected before any legal documents were issued to formally establish the town or its market. Part of the allocated area – on which seven burgage plots had been laid out (at least on a plan) – he subsequently (at some time between 1304 and 1310) regained burgages from the Abbey of Haughmond, through exchange for 4s. annual rents payable from other of his estates; this implies those burgages had not yet found tenants – for, if they had, they would have generated an income of 7s a year for the abbey and obliged Edmund to a more generous exchange. The deed of exchange described the burgages as being in the fee of the church in the 'new vill' of Ruyton. Some, however, of the building plots laid out in New Ruyton, as it was subsequently known, had already found tenants by the time that the earl, then being in Ruyton, by charter of 22 June 1309 (that date being the Sunday closest to the festival of St. John the Baptist) designated it a liber burgus; those who had already taken up plots and those who would do so in the future were assured they would hold by burgage tenure, at a 12d. rent.

This charter authorized the burgesses to have a merchant gild, which was to administer the assize of bread and ale, and its own court, to meet about every three weeks, separate from that of the manor. The burgesses were exempted from tolls anywhere on the earl's estates as well as from any feudal dues, and assigned the laws of Breteuil (in their form as developed at Hereford and Shrewsbury). A monopoly on brewing and commerce was allowed to the burgesses, and they were authorized to assign such privileges to others, which enabled the imposition of fees on such delegates; in regard to brewing – which, thanks to the river, seems to have been a significant local industry – the earl reserved the right to receive three gallons from each brew produced in the borough, as an exception to a guarantee that he would pay within forty days for any foodstuffs he had of burgesses. As further incentive to attract settlers who would take up burgages, a free air clause was also included in the charter. That Edmund hoped his borough would grow in size and population may be indicated by his preference to receive a rent from each individual burgage, rather than have the burgesses, communally, farm the borough from him for a lump sum.

In 1311, with his title to the territory of the borough secured, Edmund paid out for a licence for a Wednesday market and a five-day fair in June around the festival of St. John Baptist; the duration of the fair is another indication that the existing or projected volume of commerce warranted a longer-than-normal event. Perhaps the intent was to provide an additional outlet for trade in the products of a growing Welsh cloth-making industry, which was helping Oswestry's economy flourish. Oswestry's commercial institutions belonged to the Fitz-Alans, so Edmund would not wish Ruyton to compete directly with them; Ruyton's market was timed to take place two days apart from that at Oswestry, and its fair held in a different month to those at Oswestry. It must have been Shrewsbury that was rather the competitor from which Edmund hoped to siphon away commercial business.

However, Earl Edmund was becoming increasingly drawn into national politics and would eventually fall a victim to Roger Mortimer, who then took over the Fitz-Alan estates, not restored to the Fitz-Alan heir until Mortimer's death in 1331. Edmund's successors confirmed (1393 and 1430) the foundation charter and extracted their annual revenues from the town, but otherwise seem to have given it little attention – neither confirmation was issued at Ruyton itself, which had become a minor part of the earldom. The castle appears to have fallen into disrepair again, perhaps even been abandoned in the later fourteenth century; yet the threat, and occasionally the actuality, of Welsh raids continued to pose a problem for the townspeople and their commerce. After a period of modest growth, Ruyton settled into a gradual decline, which must have been given impetus by the assault in 1400 by Glendower, who controlled Ruyton for the next few years, and (following its recapture) by the Earl of Arundel's decision in 1407 that residents of his estates, including Ruyton, should channel their trade through Oswestry's market. The unsettled conditions during Glendower's rebellion assured the better-defended towns of Shrewsbury and Oswestry a larger role in regional commerce. In the post-medieval period Ruyton remained a borough in name, but functionally was no more than a large village.

The early fourteenth century planned town of New Ruyton spread out along the lower ground of the valley slope, closer to the river, whose course came from the north then swung south-easterly. It was laid out around a single street (now Church Street and School Road) paralleling the curving course of the river, as far south-east as the castle and church, which were adjacent to each other on the higher ground; burgage plots are particularly apparent along the eastern side of Church Street, which continued eastwards beyond Ruyton to Baschurch. Properties east of the castle remained part of the manor (Old Ruyton) and may represent pre-urban settlement. One possible spot for a marketplace is at the north end of Church Street, where it terminates at a junction with other roads from north (School Road) and west arriving from Oswestry; the post-medieval market hall is thought to have been located at that junction, and what seem to have been burgage plots extended some distance up School Road, which would place the junction at about the centre point of the planned town. Another marketplace candidate is just west of the castle, where there is a wider stretch of Church Street, into which runs a road from the south, linking to Shrewsbury, and a lesser route from the hamlet of Wykey just north of Ruyton. A two-phase development is conceivable, with the initial town and marketplace near the castle, and later expansion northwards from the junction, with an associated change in focus of the marketplace; such expansion would have been constrained by vulnerability to flooding as School Road came closer to the river, but residents engaged in brewing or tanning may have preferred plots that stretched down to the riverside. No archaeology has been undertaken that might clarify whether the town was developed on a single plan or as a phased development.