In 1772 Captain John MacDonald of Glenfinnan, Scotland, arranged passage for a large group of Scottish Catholic Highlanders to Glenaladale, his 20,000 acre estate in Tracadie, Prince Edward Island. 8th laird of Glenaladale and second in command of the Clanranald chieftans, “Captain John,” as he is remembered today, had become disenchanted with the economic policies of the post-Culloden chieftains and the climate of intolerance toward Catholic Scots. Responding to the Roman Catholic bishops of Scotland, who identified emigration as the most promising option, Captain John organized a humanitarian effort by which friends, family, and fellow Highlanders from South Uist and the mainland could make a new home in a friendlier land. In realizing this plan, Captain John was supported by the Roman Catholic Church, but in carrying out the plan, he was aided by his brother Donald, who lead the trans-Atlantic journey on his behalf, and his sister Helen (Nelly), who established and managed the Glenaladale estate single handedly for nearly 19 years. This paper presents the initial findings of archaeological investigations at the PEI Glenaladale estate, including excavations at the site of Captain John’s mansion.