Henry Bickersteth began medical studies at St. Thomas's Hospital in London but ended them to accept employment in Cape Town as hospital assistant to Dr. Samuel S. Bailey, resident surgeon of Somerset Hospital. He arrived at the Cape in December 1831, aged 17, unqualified, with a wife to support, and with no official appointment. Bailey, after supporting his assistant out of his own pocket for some time, requested the government in 1834 to give Bickersteth a salaried appointment on the full-time staff. Despite strong opposition from the medical practitioners of Cape Town, based mainly on Bickersteth's lack of medical qualifications, his appointment as hospital assistant was finalised in December 1834. Soon thereafter he volunteered to serve on the eastern frontier as staff assistant surgeon with the Seaforth Highlanders in the Sixth Frontier War, from May 1835 to April 1836. On his return to Cape Town he left for Britain to complete his medical studies at St. Thomas's Hospital. He was admitted as a member of the Royal College of Surgeons of London in January 1838 and returned to the Cape in June that year. There he resumed duty at Somerset Hospital and was licensed to practice as surgeon and accoucheur.
When Dr. Bailey retired in 1845 Bickersteth succeeded him as resident surgeon of Somerset Hospital, a post which he retained to his death in 1862. He turned it into the earliest teaching hospital at the Cape, giving lectures, conducting students round the wards, and inviting civilian and military doctors to attend his rounds and operations. During 1847 he published several case reports in the short-lived Cape Town Medical Gazette, dealing with an aneurism of the carotid artery at the root of the neck (January), an operation for empyema (April), and an operation for cataract (July). He was an early user of ether as an anaesthetic (first used at the Cape by the dentist Alfred Raymond* in 1846), performing two amputations with its help in October 1847. In 1852, and again in 1855, he was appointed to enquire into conditions at the institution for lunatics and lepers on Robben Island. In August 1853 he went overseas on sick and study leave and qualified as Doctor of Medicine (MD) at St. Andrews in Scotland. He was furthermore the first person from South Africa to be admitted, by examination, as a Fellow of the Royal College of Surgeons of London, making him the first person with a higher qualification in surgery to practice at the Cape. In 1855, when the South African Museum was formally established as a government museum, he commenced a pathological collection for it.
Bickersteth's primary preoccupation was the hospital and he worked hard to improve the quality of its service. Among many other improvements he established an outpatient section and succeeded in having the mentally ill and lepers transferred to Robben Island. His efforts over many years to have a new hospital erected eventually led to parliamentary approval of funds for this purpose in 1858. The new hospital was opened shortly after his death in 1862.
Bickersteth was a man of many talents. In addition to his surgical skill and sound knowledge of medicine he was remembered by one of his pupils, Dr. H.A. Ebden*, as a Greek scholar, poet, musician, actor, artist, and elegant writer. He served on the management committee of the South African Literary and Scientific Institution from 1852 to 1857, and published a collection of psalm and hymn tunes in Cape Town in 1858. He was married to Jane Shuter Boswell.