[3] After several years in Stornoway, Outer Hebrides, the family settled in the fishing community of Englishtown, Cape Breton Island, around 1831.

When MacAskill was approximately 14 years old he travelled on a fishing schooner from St. Anns to North Sydney and the crew took him along to a dance.

French sailors apparently taunted MacAskill to lift an anchor lying on the wharf, which was estimated to weigh 2,200–2,700 pounds (998–1,220 kg).

[1] Queen Victoria heard stories about MacAskill's great strength and invited him to appear before her to give a demonstration at Windsor Castle, after which she proclaimed him to be "the tallest, stoutest and strongest man to ever enter the palace", and presented him with two gold rings in appreciation.

[2] After a show business career demonstrating his size and strength in Europe and North America, he returned to his home community of Englishtown and purchased a gristmill, a general store and several other properties.

In the summer of 1863, MacAskill undertook a trip to the colonial capital at Halifax, where he had been planning to sell produce and purchase stock for his store that he would need for the winter season from the city's wholesalers.

[5] The Halifax Acadian Recorder of August 15, 1863, reported that "the well-known giant... was by far the tallest man in Nova Scotia, perhaps in British America" and that "his mild and gentle manner endeared him to all who had the pleasure of his acquaintance".

[3] MacAskill's presence lived on in Englishtown for many years where his timber-frame house sat on the edge of Kelly's Mountain, overlooking St. Anns Harbour.

Some of MacAskill's original personal effects from his house, including a bed frame, clothes and chair were removed for preservation and displayed for many years during the mid-20th century at the nearby Gaelic College of Celtic Arts and Crafts.

Despite the relatively short crossing, it became the busiest ferry service in Nova Scotia, carrying hundreds of thousands of vacationers and residents every year until its replacement in 2008 by the newly built vessel Torquil MacLean.