William H. Reagan was the son of John Reagan (Regan) and Julia Grady, both natives of Ireland. John Reagan was born around 1807, the son of Christopher Reagan (born 1775) and Honora Murray (1777-1870), who emigrated as to the United States as a family after 1819. John married Julia Grady, born around 1808, and the couple settled in Ansonia, then a village in the town of Darby, Connecticut, where their children were born:
Between 1850 and 1855, both John and Julia died, leaving seven children without home or support. Having learned that their grandparents, Christopher and Honora Reagan, were living in North Adams, Massachusetts, the children set out on foot, making their way up the Connecticut River to Greenfield, Massachusetts, then over the Hoosac Range via the Mohawk Trail to North Adams, where they located their grandparents.
William H. Reagan is listed in census records as an engineer (1880) and shipping clerk (1900). In 1866 he married Caroline O. Newcomb (1849-ca. 1922), a native of New York State, daughter of Cyrenius William Newcomb, shoemaker, and Elizabeth Adaline "Betsey" Chase. The couple's first two children were born in New York, the third (Bessie) in Vermont; around 1875 they settled in North Adams, where the remaining children were born. Their nine children were:
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