Soon after his arrival in Canada, Hugh became part of the militia at York (Toronto), and by 1825 was also beginning his involvement in the shipping business by having the steamer Canada constructed for the York–Hamilton–Niagara run.
After settling in Canada, Hugh quickly became affiliated with the local defense forces in Toronto and began to explore business opportunities in the shipping sector, which ultimately led to the construction of a steamship named Canada for use on the York–Hamilton–Niagara route in 1825.