Ryde Castle was built in 1833 for Jonathan Dashwood, brother of Thomas Dashwood, builder of much of Ryde, as a private residence. For sixty years, only the central part of the building existed, and entry was via the impressive gateway still in existence on Dover Street. Just inside this gateway was a complete turning circle for carriages. This was the first building to be erected on what was known as The Duver, an area of sand dunes which stretched along the seafront. At the time, what is now Dover Street was known as Wellington Street, which can be seen from an 1833 map in Sheridan’s Guide to the Isle of Wight. The name was changed from Wellington Street within the next couple of years.
The houses to the East of Ryde Castle were mostly built from 1843 onwards, and Ryde Esplanade was laid out in 1855/56. Although Ryde Castle was purchased in 1843 by Rev John Orde, of Basingstoke, as with many of the large houses in Ryde at the time, the Castle was let for the season to a succession of distinguished visitors. In 1841, Thomas Duffield, esq, MP (for Abingdon) and family, in 1844, the Countess of Craven, followed in 1845 by The Right Hon Lord and Lady Henniker, MP, (for East Suffolk) and Thomas Chamberlayne and family. Thomas Chamberlayne was an English cricketer and yachtsman, who was High Sheriff for Hampshire in 1833. His yacht, the Arrow, took part in the inaugural America’s Cup race in 1851. In February, 1848, Sir Thomas Cotton Sheppard, Lady Sheppard and establishment, took Ryde Castle for six months. Sadly, Sir Thomas died here, aged 63, on April 5th of that year. The Hampshire Telegraph, of Saturday, April 8th, 1848, records: ‘At the Castle, Ryde, Isle of Wight, in the 64th year of his age, Sir Thomas Cotton Sheppard, Bart., of Thornton, Buckinghamshire, and Crakemarsh-Hall, Staffordshire.’
In May, 1849, Lord Rivers took Ryde Castle for three months. Mr and Lady Orde were still the owners of Ryde Castle in 1849, when their son was killed in a riding accident, and the property was sold after Lady Orde’s death in 1852.
In 1895, the then owner of Ryde Castle, Colonel Cradock, extended the house to include a large dining room, 30 feet by 20 feet. During WWI, he allowed Ryde Castle to be used as a Red Cross Hospital, and casuality lists were released in the local press.
Around 1930, Ryde Castle became a hotel, and shortly afterwards one of the bars became known as The Hunter’s Den. The Rolling Stones stayed at Ryde Castle in March 1964, when they played two gigs at Ryde Pavilion.