[1] 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 settled by 1822.

Henry was educated in Guernsey and at the Wolfville Academy (today Acadia University), and served 1853-69 as a lieutenant-captain in the Canadian Militia during the Fenian raids.

He promoted a large number of public and infrastructure works for Cape Breton, including the first marine railway, the first steamers from Boston, numerous wharves and warehouses, as well as post offices and lighthouses, and the bridge and railroad to Arichat, and he was instrumental in negotiating favourable trading terms for the Dominion with Norway and the West Indies.

Henry Paint's long life is exceptionally well documented for the period, largely from letters written in his old age to his grandchildren, a selection of which were published in 2005.

His elder daughter, Flora St Clair, married Sir Charles's first cousin, Theodore Mander, builder of Wightwick Manor, one of the most notable Arts and Crafts movement houses in England, owned since 1937 by the National Trust.