This is one of a group of companion portraits of the Wyndham family painted by Highmore in the 1740s. The others are listed by A.S. Lewis in the catalogue of her 1975 Harvard university Ph.D. thesis, Joseph Highmore: 1692-1780, University Microfilms International, Ann Arbor, 1980, as follows: Henry Wyndham, Arm. (1709-1722), first of the close, Salisbury, and subsequently of St. Edmund's College, Salisbury, signed and dated 1743, 50 x 40in., Yale University Art Gallery (Lewis, op. cit., pp. 517-8 no. 194, repro. fig. 128); Arundel Penruddocke (d. 1780), married Henry Wyndham 1735, signed and dated 1748 (perhaps a misreading for 1743), 38 x 50in., sold Compton Park, Salisbury, by Robinson, Fisher and Harding, 12-13 November 1930, no. 45 (Lewis, op. cit, p. 518, no. 195; possibly to be identified with her no. 196, now in the British Embassy, Lima, and said to measure 64 x 63in., perhaps including frame, though another distinct portrait of Arundel is recorded by a photograph in the Witt Library, as 38 x 50in., repro. Connoisseur, August 1918); Mrs. Henry Wyndham with her daughter Laetitia (who married Sir William P.A. à Court, Bt.), in a private collection, Ann Arbor (Lewis, op. cit, p. 519 no. 197, repro. fig. 129); and Henry Penruddocke Wyndham and Wadham Wyndham as children, playing on a large rock, signed and dated 1743, and inscribed in the same way as the present picture, probably, according to Lewis, by the artist, 50 x 40in. (Lewis, op. cit., p. 520 no. 198). Highmore also painted a portrait of Arundel's brother Charles Penruddocke (1708-1769), signed and dated 1743, 50 x 40in., now in the Yale Centre for British Art, Paul Mellon Collection (Lewis, op. cit., p. 471 no. 132, repro. fig. 91).
Henry Penruddocke Wyndham (1736-1819) and his brother Wadham were the sons of Henry Wyndham (1709-1788) and his wife Arundel daughter of Thomas Penruddocke (1678-1741) of Compton Chamberlayne, Wiltshire. Henry Wyndham was a noted topographer, especially in Wiltshire and Wales. In 1768 he married Caroline, daughter and heir of Edmund Hearst, of the Close, Salisbury. He became an F.S.A. in 1777 and an F.R.S. in 1783, Mayor of Salisbury in 1770, Sheriff of Wiltshire in 1772 and was M.P. for Wiltshire between 1795 and 1812. He was succeeded by his son, Wadham.