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.
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".