GILDERSLEEVE, OVERTON SMITH, lawyer, businessman, and politician; b. 13 Jan. 1825 at Kingston, Upper Canada, eldest of the eight children of Sarah Finkle and Henry Gildersleeve; d. 9 March 1864 at Kingston. He married Louisa Anne, daughter of William Henry Draper*, 16 Aug. 1850; there were no children.

Henry Gildersleeve arrived in Kingston from Gildersleeve (part of Portland, Conn.) in 1816, and developed a flourishing shipping and shipbuilding business. He helped construct the Frontenac, the first steamboat on Lake Ontario, in 1816, and is sometimes called “the father of steam navigation on the Lakes.” Overton Smith Gildersleeve was educated in Kingston. He took up the study of law in 1843, was called to the bar in 1849, and began practising in Kingston in 1850. Henry Gildersleeve died 1 Oct. 1851, four months after the death of Overton’s young wife, and at age 26 Overton became the head of the family shipping business, holding a majority of the stock in each ship, and the head of a household consisting of his mother, two sisters, and two brothers. He also succeeded his father as a director of the Kingston Marine Railway Company; it built all types of vessels for lake, river, and ocean traffic, and had an iron foundry, a sawmill, a hotel, and extensive wharfage rights.

With the launching of the Bay of Quinte in April 1852, Gildersleeve had three steamboats operating between Bay of Quinte ports and Cape Vincent (N.Y.). He had also taken his father’s place, with John Counter and others, in the promotion of the Wolfe Island Railway and Canal Company which was expected to provide a shorter and more protected route between Kingston and Cape Vincent. The canal was completed in 1857; it continued to be used until 1890, but it carried little traffic and was not a profitable venture.

Competition from railways began, by the latter part of the 1850s, to affect the shipping business which had earlier undergone a period of great expansion. Rivalry between railways and steamboats led to competition between boatlines for passengers. In June 1854, for example, Gildersleeve engaged in racing and rate-cutting to force Belleville competitors to withdraw their boat within a month. Usually he offered passage between Kingston and Belleville, including stateroom and berth, for 5s., but during one season he provided the same service for 15d. By 1860 Gildersleeve was offering a round trip three-day excursion to Quebec City, with a quadrille band on board, for a special fare of $15.50. Similar excursions were conducted to other river and lake ports.

With the decline in lake traffic Gildersleeve joined John Hamilton* in re-forming Hamilton’s Royal Mail Line and they became the principal stockholders in the new Canadian Inland Navigation Company. Gildersleeve and Hamilton bought up other steamers for service on their run between Hamilton, Toronto, Kingston, and Montreal. Gildersleeve was also a promoter of branch railways in this period – the Cataraqui and Peterborough incorporated in 1852 and the Kingston and Newburgh Railway in 1856.

Elected alderman in Kingston in 1854, Gildersleeve replaced Counter as mayor in June 1855 when Counter was forced to resign. Gildersleeve was elected mayor in 1861. In politics he was a Liberal, actively supporting Oliver Mowat* in the elections for the Legislative Assembly in 1861 and running unsuccessfully against John A. Macdonald* for the Kingston seat in 1863. On his death in 1864 his brother, and law partner since 1859, Charles Fuller Gildersleeve, took over the family business.

Margaret S. Angus