[2][3] MacAskill was born and raised in the seaside town of St. Peter's, Nova Scotia, where he learned to sail as a young child.
Alongside his photography career, MacAskill took part in recreational sailing and yacht racing.
[2] MacAskill published two books of photography: Out of Halifax in 1937 and Lure of the Sea in 1951.
[4] He was elected a fellow of the Photographers Society of America in 1954, and ran a photography studio in Halifax until his death from cerebral hemorrhage in 1956.
[2][3] MacAskill's wife, Elva (1891-1968) continued to run the studio until eight years after his death.