He studied law with Matthew Crooks Cameron, was called to the bar in 1875 and set up practice in Toronto.

He authored several books: The Irish problem as viewed by a citizen of the Empire (1887); The New Empire - reflections upon its origin and constitution and its relation to the great republic (1891), in which he reprinted views he had previously presented in columns in the Toronto Week.

[1] Shortly after his mayoralty, Toronto began to use cumulative voting to elect the board of control.

Howland was appointed a Companion of the Order of St Michael and St George (CMG) during the visit to Toronto of the Duke and Duchess of Cornwall and York (later King George V and Queen Mary) in October 1901.

[3] His older brother William Holmes Howland also served as 25th Mayor of Toronto a decade and a half earlier.