In 1899, Charlotte and her husband John Kenelm Wingfield Digby founded Sherborne School for Girls. The school opened on 20 September 1899 at Ramsam House on Greenhill with just 14 pupils, including five little boys.

Charlotte was also a founder and governor of Headington School for Girls in Oxford, a governor of Foster’s and Lord Digby’s Schools in Sherborne, and a life governor of the Yeatman Hospital. She worked for the Church Missionary Society, visiting mission stations in Central Africa, South China, and Palestine.

The following obituary was published in the Western Gazette on 8 February 1935:
‘LATE MRS J.K.D. WINGFIELD DIGBY. WORK FOR EDUCATION AND MISSIONS.
The death of Mrs Charlotte Kathleen Wingfield Digby, at The Court, Chetnole, on Tuesday, ended a remarkable life, which has left a permanent influence on educational and other work over a wide field.
Mrs Digby, who was 71 years of age, was a daughter of the late Mr and Mrs William John Digby, of Moat Lodge, Co. Galway, Ireland. Her husband, Mr John Kenelm Wingfield Digby, J.P., of Sherborne Castle, who was formerly M.P. for North Dorset, died in 1904.
Mrs Digby was a lady of generous sympathies and a devoted worker in religious and educational movements. She had been ill for many months, and her death is a great loss to the causes she had so much at heart.
She manifested a deep and practical interest in missionary work, and the activities of the Church overseaas, particularly in the Church Missionary Society. Among her extensive travels in many parts of the world were her visits to the C.M.S. Mission Stations in Central Africa, South China, and Palestine. The first C.M.S. misssionary pageant held in Sherborne in 1901 owed its success largely to the thoroughness with which she organised it, and such results became customary in the many directions in which she extended her inerest and support.
EDUCATIONAL ACTIVITIES.
Her interest in and work for education was perhaps the outstanding feature of her life’s work, and Sherborne’s prominent position as an educational centre owes a very great deal to her enterprise her enthusiastic and zealouse service, and her inspiring example. She was the founder, with her husband, in 1899, of Sherborne School for Girls, which has grown from small beginnings at a house on Greenhill to be one of the finest and best-known girls’ schools in the country. She took a leading part in guiding its destinies, and was largely responsible for the remarkable progress of the foundation, which is a worthy memorial to her life’s activity in the sphere of education. The site of the present school was the gift of her husband. She was also a founder and governor of the Headington School for Girls at Oxford, and a Governor of Foster’s and Lord Digby’s School, Sherbonre.
GIFT TO CHETNOLE.
Mrs Digby took a very great interest in the parochial life of Chetnole, and an example of her generosity in that direction was her gift of a Village Hall in memory of her daughter, Miss Dorothy Wingfield Digby, a few years ago.
Mrs Digby’s name will always be associated with Sherborne, in which, through all her life in this part of the country, she had taken a deep interest. She was a life Governor of the Yeatman Hospital and a valued supporter of many institutions, which have lost a generous benefactor by her death.
She was a remarkable personality, tireless in her energy, and with a mental equipment that combined high intellectual gifts with an usual capacity for organisation and wise guidance. In spite of her illness, her interest in and eagerness to help any deserving causes continued until the end.
She leaves four sons – the eldest of whom is Lieut.-Colonel F.J.B. Wingfield Digby, D.S.O., of Sherborne Castle – and one daughter.
A memorial service will be held in Sherborne Abbey on Friday at 2.30 p.m., followed by the funeral, for relatives only, at Castleton.’
Rachel Hassall