At the time of the rebellion Mr. Howland had become a prosperous man, and his operations were still extending. There was a good deal of feeling in his neighbourhood that Mr. Mackenzie had been badly used by the Family Compact Party, and that many reforms were needed in the body politic. A deputation of these malcontents waited upon Mr. Howland, and endeavoured to enlist him in the insurrection which broke out in December, 1837. Mr. Howland, however, was too wise to connect himself with an enterprise which never had any chance of being permanently successful. Moreover, he had not then been naturalized, and as an alien, he did not deem that he had any right to engage in political contests of any kind. His naturalization took place soon after the Union of the Provinces. He did not, however, take any very active part in the periodical election contests until the general election of 1848, when Mr. James Hervey Price successfully opposed the Conservative candidate in the West Riding of the county of York, just prior to the formation of the second Baldwin-Lafontaine Administration. Mr. Howland's sympathies were with the Reform Party, and he worked hard to secure Mr. Price's return. He thenceforward took a not inactive part in all the election contests, and always on the side of the Reform Party, with which he became identified. He had meanwhile removed to Toronto, and had embarked in a large wholesale business, with large interests in the produce, milling, and other branches of trade. Among his commercial friends he enjoyed a high reputation for capacity and genuine business worth. He became a magnate among the wholesale merchants of Toronto, and amassed a fine fortune which has steadily augmented. His political views became more pronounced, and he supported the wing of the Reform Party led by Mr. Brown after the disruption in its ranks. He soon came to be looked upon as an eligible candidate for Parliament. His eligibility was proved at the general elections of 1857, when he was returned to the Assembly by the constituency of West York, in which he had resided for many years. He continued to sit for that constituency during the whole of his Parliamentary career, which was terminated by his acceptance, in 1868, of the Lieutenant-Governorship of Ontario.