DeWolf was born in Lyme, Connecticut on October 17, 1744 in the prominent DeWolf family. He was a son of Simeon DeWolf and Parnell DeWolf, who emigrated to Nova Scotia. His paternal grandparents were Benjamin DeWolf and Susannah DeWolf of Lyme and his maternal grandparents were John Kirtland and Lydia Kirtland of Saybrook, Connecticut. His paternal grandfather was the younger brother of Charles DeWolf.
Career
DeWolf had received a number of large land grants near Windsor. He represented Hants County in the Nova Scotia House of Assembly from 1783 to 1798. In 1788, he was named a justice of the peace. DeWolf served as High Sheriff for Hants County. In the autumn of 1780, DeWolf offered a "handsome reward" to anyone "securing a Negro boy named 'Mungo', 'about fourteen years old and well built'." His account books showed the sales in the West Indies of slaves from Hants County. DeWolf was also said to have given his slaves their freedom, but they chose to remain in his employ.
Personal life
On 16 March 1769, he married Rachel Otis, a daughter of Dr. Ephraim Otis of Scituate, Massachusetts, and sister of Susannah Haliburton. Together, they were the parents of:
Sarah Hersey Otis DeWolf, who married Maj. Nathaniel Ray Thomas Jr., the Collector of Customs at Windsor who was a son of prominent Loyalist Nathaniel Ray Thomas, and a first cousin of Lady Frances Wentworth.
Harriet Sophia DeWolf, who married Rev. William Colsell King, Rector of Windsor, in 1799.
DeWolf died on 1 September 1819 in Windsor, one of the oldest magistrates in the Province and, by that point, an inhabitant of Windsor for upwards of fifty years.
Descendants
Through his eldest daughter Sarah, he was a grandfather of Sarah Rachel Thomas, who married Judge Lewis Morris Wilkins. Through his surviving daughter Rachel, he was a grandfather of Sarah Rachel Fraser, who married Hon. Charles Stephen Gore ; James DeWolf Fraser, who married Catharine Prescott ; Harriet Amelia Fraser, who married Col. Dixon in 1826; Amelia Isabella Fraser ; Frances Mary Fraser ; Dr. Benjamin DeWolf Fraser ; Catharine Fraser, who married the Rev. Thomas G. Suther, Bishop of Aberdeen and Orkney; and Mary Hulbert Fraser.