From the death of Berkhamsted Castle’s last noble resident, Cecily, Duchess of York (1415–1495). the Castle fell into ruin and was all but forgotten as a royal landholding.
In 1616, Berkhamsted was visited by Charles, Prince of Wales and Duke of Cornwall – the future King Charles I. In this time before the outbreak of the Civil War, the townsfolk were largely welcoming of the royal visitor.
The 16-year-old prince was met by 20 mounted townsmen and escorted down Grubb’s Lane (now Chesham Road) to Castle Street. There, he was welcomed by the staff and students of Berkhamsted School, where he heard “an oration pronounced by one of the schollers of the free schole.”
The prince then continued to Berkhamsted Place, which he had leased to his former tutor, Richard Murray, They enjoyed an afternoon’s hunting together, and Charles killed a deer, which he then donated to the townsfolk.
Only a few years later, the Civil War erupted, and Berkhamsted was caught up in the conflict. The townsfolk’s sympathies mostly lay with Cromwell and the Parliamentarians, but it was still a town divided. The Earl of Bridgewater was a Royalist supporter, and paid the price when Ashridge House was looted by Cromwell’s soldiers. Richard Murray at Berkhamsted Place was also a Royalist. Two of his sons, James and John Murray, were apparently died in the conflict, and their death is commemorated by a marble memorial in St Peter’s Church. Notably, his daughter Anne took part in a plot to smuggle the young Duke of York (later King James II) to safety, Berkhamsted was also home to one of Cromwell’s most feared henchmen, Daniel Axtell, who rose to become a general in the Roundhead army.
The Civil War culminated in the execution of Charles in 1649. In only a few years, public opinion had turned against the king. Charles was the last Duke of Cornwall to visit the town for a long time – the next time the town was to welcome a Duke of Cornwall was to be 1935, on the visit of Edward, Prince of Wales and the future King Edward VIII,