The Greg family originated in Ayr, Scotland, but John Greg (1693-1783) settled in Belfast in 1715. He had two sons. The elder, John (1716-1795) went to the West Indies in 1765, married there and became the first Government Commissioner for the sale of land. He had two estates in Dominica, Hertford, of 250 acres, owned jointly with Mr. Jennett, and Hillsborough of 120 cultivated acres in the parish of St. Joseph. This latter was originally named Layou, but received its new title in honour of Viscount Hillsborough (later 1st Marquis of Downshire) a friend of the Greg family. John Greg later sold Hertford estate, but in 1773 Mrs. Greg (neé Catherine Henderson) inherited Cane Garden estate, St. Vincent, from her mother.

His brother Thomas Greg (1718-1796) also owned an estate in Dominica, in partnership with Waddell Cunningham. This adjoined Hertford and was called Belfast. Thomas Greg married Elizabeth Hyde and has 13 children: he died in 1796, leaving his youngest son Cunningham as residuary legatee, and he and Waddell Cunningham sold the Belfast estate for £17,000.

On 10th June 1795, John Greg died in England. He bequeathed his West Indian properties to his nephews Thomas and Samuel, the sixth and ninth children of his brother Thomas, with a life interest to his widow, Catherine. She died at Hampton, aged 82, on 22nd November 1819, and is buried with her husband in a pyramidal tomb, the source of local legends, in the churchyard there.

Thomas, who died in 1832, conveyed his share to Samuel in return for an annuity of £1,500, but the estate more than repaid this in the prosperous period of the 1820s. The Gregs did not administer the estate directly, but through a local agent and a resident manager.

Samuel Greg had settled at Quarry Bank, Manchester, and was a prosperous merchant. The 1830s bought many changes: the abolition of slavery in 1833, the death of Samuel Greg in 1834, and a severe hurricane in Dominica in September of the same year. The damage was estimated at £5,000-£7,000, but new buildings were erected and the estate work resumed.

Samuel Greg had eleven children, including five sons: Thomas; Robert Hyde, economist and antiquary; John; Samuel, mill owner and philanthropist; William Rathbone, political and philosophical writer. The last of these was named after William Rathbone (1757-1809) merchant and reformer. The Greg and Rathbone families were close friends, and Samuel Greg’s daughter Elizabeth married William Rathbone junior (1787-1868); their grand-daughter was Eleanor Rathbone, M.P.

On Samuel’s death the West Indian Estates passed to his eldest son Thomas, but he survived his father by only five years, and they became the joint property of the remaining brothers. Robert Hyde Greg (1795-1875) bought out his brother Samuel’s life interest in 1845, and twenty years later passed the estates to his son Robert Philips Greg (1826-1906), who in turn bought out the shares of his uncles John (1868) and William (1875) and in 1870 sold the Cane Garden estate. On 31st December 1894 R.P. Greg sold all his interests in Hillsborough to his nephew John Tylston Greg, who decided to supervise it personally, and continued to run the estate until 1928 when he sold it and returned to England to spend the rest of his life in Oxford in a house he named Hillsborough.