The exact age of the Kings Head is not known, but it was certainly in existence as a coaching inn in the middle of the fourteenth century. Records show that in 1550, it was owned by Robert Strange of Cirencester, a clothier and high Bailiff in 1553 and it was thought that he was also the High Sheriff of Gloucester. He died in 1588 and since that time much of the town's and indeed the county's history has developed around it. The Kings Head was passed on with twelve other properties to his great grandson Robert Strange of Somerford Keynes. Robert Strange died in 1654 and is commemorated by large marble monument in the village church. As young Robert died unmarried, his estates were divided between his sisters, and the youngest Katherine, wife of Sir Robert Jocelyn of Sawbridge-worth, took as her share Chesterton, Watermoor House and The Kings Head with the Manor of Shorncote. Her son, Sir Strange Jocelyn sold Shorncote in 1714 but it is not known how long the family kept the Kings Head. It is known however, that in 1893 the Kings Head was owned by the Right Hon Seymour Henry Earl Bathurst and it remained in his ownership until July 1935.
The Kings Head is now listed as a building of special architectural and historical interest.
On one occasion at least the Kings Head was the scene of an event which was to affect the destiny of the entire nation. August 1642, Giles Lord Chandos came to Cirencester with the commission of Array to enlist men for King Charles I. The town at the time violently Parliamentarian did not take kindly to his Lordship's visit. The population rose against him, killing some of his company and smashing and burning his coach in the Market Place. Lord Chandos made his escape with great difficulty to the nearby Kings Head and was thus spared the fate of his companions. This incident which occurred outside the Kings Head is depicted in a famous painting by John Beecham - an artist of great repute - a copy of which occupies pride of place in the reception of the hotel.
Coming forward to the 18th century, the scant references to the Kings Head refer to cock fighting in 1767 and moving forward to the end to the end of the century, the first identified record of the inn on plan dates from Hall and Sons map of Cirencester from 1795. The plan depicts the old Market Place with its two rows of buildings sandwiched between the north and south side of the market. Taken as a whole, it is hazardous to attribute too much accuracy to the 1795 plan but equally it provides some supporting evidence for the basic footprint of the Kings Head in the late 18th century.
An illustration of the market place by John Burden attributed to 1804, just captures the frontage of the Kings Head and provides a tantalising glimpse of its early 19th century appearance. The key points to note are the similarity of its mansard-style roof, three story height and general proportions to its present appearance.