DeWolf was born in Lyme, Connecticut on October 17, 1744 in the prominent DeWolf family. He was a son of Simeon DeWolf (1719–1780) and Parnell (née Kirtland) DeWolf (1724–1827), who emigrated to Nova Scotia.[1]
His paternal grandparents were Benjamin DeWolf and Susannah (née Douglas) DeWolf of Lyme and his maternal grandparents were John Kirtland and Lydia (née Belden) Kirtland of Saybrook, Connecticut.[1]
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'."[3] His account books showed the sales in the West Indies of slaves from Hants County.[3] DeWolf was also said to have given his slaves their freedom, but they chose to remain in his employ.[citation needed]
Sarah Hersey Otis DeWolf (b. 1770), 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 (who was known for her affair with Price William Henry, later King William IV).[7]
Rachel Hersey DeWolf (1772–1772), who died in infancy.[1]
Rachel Otis DeWolf (1773–1815), who married James Fraser (c. 1760–1822) in 1802. Fraser, who was born in Inverness, Scotland, served in the New Brunswick assembly and the Nova Scotia Council.[1]
John DeWolf (1775–1775), who died in childbirth.[1]
Susanna Isabella DeWolf (1776–1777), who died young.[1]
Frances Mary DeWolf (1778–1791), who died young.[1]
Isabella Amelia DeWolf (b. 1779), who married Capt. John McKay of 27th Regiment in 1821.[1]
Harriet Sophia DeWolf (b. 1781), who married Rev. William Colsell King, Rector of Windsor, in 1799.[1][8]
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.[9]