Henry Hakewell was a pupil of John Yenn, R.A., and also studied at the Royal Academy, where in 1790 he was awarded a silver medal for a drawing of an aspect of Somerset House. He began work on a country mansion and eventually had a large and flourishing practice, mostly concerned with country houses.
In 1809 Henry was appointed architect to Rugby School, where the gothic buildings and chapel are his designs. He also did work for the Radcliffe trustees at Oxford and the Middle Temple.
In his private life, on 14 November 1804 Henry Hakewell married Anne Sarah Frith, daughter of Rev. Edward Frith of North Cray, Kent. They had seven children including two sons who were also architects: John Henry Hakewill (1811-1880), and Edward Charles Hakewill(1812-1872).