Detailed biographies of John and Helen MacDonald are available in the Dictionary of Canadian Biography Online.
29 September 1742 — John MacDonald is born in Glenaladale, Scotland, to parents Alexander MacDonald of Glenaladale and Margaret MacDonell.
1745 — John MacDonald's father supports Prince Charles Edward Stuart in the Jacobite rebellion and participates in the battle of Culloden.
1745 — After the rebellion, the MacDonalds suffer reprisals at the hands of the British.
c. 1750 — John MacDonald's younger sister and future estate manager Helen (Nelly) MacDonald is born.
1756 — John MacDonald departs for the continent to study at a Catholic Seminary in Regensburg.
1761 — Alexander MacDonald dies, making John MacDonald the eighth laird of Glenaladale. He returns to Scotland to manage his family's estate.
1763-1766 (Date undetermined) — John MacDonald marries Isabella Gordon of Wardhouse, Aberdeenshire, Scotland. Isabella dies shortly after giving birth to their first child, who also dies several months later.
1767 — Sixty-four out of sixty-seven lots surveyed by Samuel Holland on St John's Island are assigned to British land proprietors, mostly military officers and gentry.
28 June 1769 — The Island of St. John is granted its own government, separate from Nova Scotia.
1770 — Colin MacDonald of Boisdale evokes measures designed to force his tenants at South Uist, Scotland, to abandon their Catholic faith. The Scottish Catholic Church approaches John MacDonald to coordinate the tenants' planned emigration to North America.
1770 — Bishop Hay of the Scottish Catholic Church opens negotiations with the Lord Advocate of Scotland, James Montgomery, who agrees to sell one of his lots on St. John's Island to John MacDonald.
Spring 1771 — Donald MacDonald, younger brother of John MacDonald, leads an expedition of a dozen men to St. John's Island to inspect the land and sow grain in preparation for the pending emigration from Scotland.
May 1772 — Under the leadership of Donald MacDonald, and accompanied by sisters Helen and Margaret (Peggy), 210 emigrants embark from Scotland aboard The Alexander for their new home on St. John's Island.
1773 — John MacDonald leaves Scotland for St. John's Island, travelling via Philadelphia and Boston to secure supplies for his new settlement.
June 1775 — The American Revolutionary War begins. John MacDonald receives a commission as a captain in the second battalion of His Majesty's 84th Royal Highland Regiment of Emigrants, which was stationed for most of the war in Halifax.
Summer 1776 — MacDonald returns to St. John's Island to address difficulties with his tenants.
1780-1781 (Date undetermined) — Donald MacDonald dies.
November 1781 — During John MacDonald's absence, Governor Walter Patterson seizes and sells lots of absentee proprietors, including Lot 35, which John MacDonald had planned to buy.
1782 — MacDonald travels to London to represent land proprietors and make their case to the Crown against the 1781 Land sales.
1787 — Edmund Fanning replaces Walter Patterson as governor while John MacDonald remains in London presenting his case against the former governor to the Crown.
1792 — Helen MacDonald marries Ronald MacDonald of Grand Tracadie shortly before her brother, John MacDonald, returns to the Island.
1792 — John MacDonald marries his second wife, Margaret MacDonald of Guernish, Scotland, and returns with her to his estate on the Island.
1792 — MacDonald officially acquires Lot 35, the long-coveted lot adjacent to his own.
1795 — John MacDonald is appointed adjutant general of the militia by Governor Edmund Fanning.
1797 — The Island legislative assembly adopts a series of detailed resolutions aimed at collecting the quitrents owed by proprietors.
c. 1803 — Helen MacDonald dies on St. John's Island, which by this time had been renamed Prince Edward Island.
1805— Bogged down with his quitrent arrears, John MacDonald travels to England where his debts are forgiven by the Crown.
28 December 1810 — John MacDonald dies at the age of 68.