Windsor, United Kingdom

The settlement at Old Windsor largely transferred to New Windsor during the 12th century, which required the substantial planning and setting out of the new town, including its parish church, marketplace, and burgage plots. There was a second development phase after the Anarchy, the civil war of King Stephen's reign, when its hospital (c. 1160, later dedicated to St Peter), a hermitage (c. 1160, dedicated to St Leonard) and Thames bridge (c. 1173), came into existence. At about the same time, the castle was rebuilt in stone. Windsor Bridge is the earliest bridge on the Thames between Staines and Reading, built (and owned by the Crown) at a time when bridge building was rare; it was first documented in 1191 but had probably been built, according to the Pipe rolls, in 1173. It played an important part in the national road system, before the construction of the Great West Road in c. 1230, linking London with Reading and Winchester. By directing traffic into the new town, it underpinned the success of New Windsor's fledgling economy.

The town of New Windsor, as an ancient demesne of the Crown, was a privileged settlement from the start, apparently having the rights of a free borough, for which other towns had to pay substantial fees to the king. It had a merchant guild, a part of civic government, in 1260, this body sometimes incorrectly confused with the 14th century religious Fraternity of the Holy Trinity, based in the parish church.

After receiving its first charter confirming its royal borough status in 1277, Windsor was briefly named as the chief town of the county. Somewhat unusually, however, this charter gave no new rights or privileges, seeming simply to codify rights enjoyed over many years before.

Windsor's position as chief town of Berkshire was short-lived, however, as people found it difficult to reach. Wallingford took over this position in the early 14th century. As a self-governing town Windsor enjoyed a number of freedoms unavailable to other towns, including the right to convene a court of record, the right to inherit land (burgage plots), and the right to elect its corporation. The town accounts of the 16th century survive in part, although most of the once substantial borough archive, dating back to the late 12th century, was destroyed, probably in the late 17th century.

New Windsor was a nationally significant town in the Middle Ages, certainly one of the fifty wealthiest towns in the country by 1332. Its prosperity came from its close association with the royal household. The repeated investment in the castle brought London merchants (goldsmiths, vintners, spicers and mercers) to the town in the late 13th century and provided much employment for townsmen. The development of the castle under Edward III, between 1350 and 1368, was the largest secular building project in England of the Middle Ages, and many Windsor people worked on this project, again bringing great wealth to the town. Although the Black Death in 1348 had reduced some towns' populations by up to 50%, in Windsor the building projects of Edward III brought money to the town, and possibly its population doubled: this was a 'boom' time for the local economy. People came to the town from every part of the country, and from continental Europe. The poet Geoffrey Chaucer held the honorific post of Clerk of the Works at Windsor Castle in 1391, although there is no record that he ever visited the town.

The development of the castle continued in the late 15th century with the rebuilding of St George's Chapel as a royal mausoleum, as Westminster Abbey was considered full and unable to accommodate further royal burials. With this Windsor became a major pilgrimage destination, particularly for Londoners. Pilgrims came to touch the royal shrine of the murdered Henry VI, the fragment of the True Cross and other important relics. Visits to the chapel were probably combined with a visit to the important nearby Marian shrine and college at Eton, founded by Henry VI in 1440, and dedicated to the Assumption; which is now Eton College. Pilgrims came with substantial sums to spend, providing a substantial boost to the town's economy. From perhaps two or three named inns in the late 15th century, some 30 can be identified a century later. The town again grew in wealth. For London pilgrims, Windsor was probably – but briefly – of greater importance than Canterbury and the shrine of that city's patron saint Thomas Becket.