Henry Paint was the son of Nicholas Paint, JP, by Mary Le Messurier, both of old Guernsey families which had been trading with Nova Scotia since at least the mid-18th century; a 'Paint Island', off Canso, is recorded in 1750.Expeditions of Honour: the journal of John Salusbury in Halifax, Nova Scotia, 1749–53, p. 87, ed. R. Rompkey, 1982 In 1817 his father, a merchant shipowner and agent at Arichat, Nova Scotia, petitioned for land grants at Belle Vue on the Strait of Canso, where he built a stone house and had settled by 1822. Henry was educated in Guernsey and at the Wolfville Academy (today Acadia University), and served as a lieutenant-captain in the Canadian Militia during the Fenian raids.
