Comprises: letters to his sister Elizabeth Wiles, 16 June 1793; to his sister Ann Wiles, [1794?]-4 October 1843; to his brother James Wiles, 17 August [1831?]; to his son John Wiles, 14 January 1842-23 October 1844; bills of exchange 10 May 1844 and 29 April 1845. Letter of [1794] to sister Ann is copy of an essay titled ‘On the pleasures and advantages of religion’ from The Rambler magazine. Letter of 25 June 1895 from Caroline Bay, Barbadoes [Barbados] to sister Ann describes tribulations of his voyage to the Caribbean. After a long gap in letters, the correspondence resumes on 7 Mar. 1831 with letter to his son, John, discussing the coffee market and the crop at Monmouth Mount [a plantation owned by James Wiles with enslaved labour]. Letter of 8 July 1832 to sister Ann discusses the [slave] rebellion and emancipation in Jamaica (referred to in the letters as ‘negroes’), with an extract from a sermon of a ‘dissenting Minister’ beginning ‘If Christianity meddles not with the civil relations of Master and Slave ...’ Letter of 20 Jan. 1843 discusses brother John’s death (died 1842), and his claim to Mount Teviot estate where Henry was a partner. Letter of 4 Oct. 1843 to sister Ann gives description of Manheim estate, referred to as ‘our native place’, and the labourers there.