At the age of seventeen, Henry Wood Booth met Clara Louise Irene Gagnier, the eldest daughter of Maria Martel and Charles Gagnier, also of St. Catharines. They were married on May 18, 1858, at Trinity Church in Toronto. Henry and Clara had ten children: Charles Henry, Alice Martel, Grace, George Gough, Edmund Wood, Theodora Marianne, Adelaide Clara Louise, Ralph Harman, Roland Bucer, and Bertha Beatrice.

In his twenties, Booth was active in temperance work, publishing in several news and temperance papers in St. Catharines, Ontario. At the same time, he also worked for winegrowers in the state of New York, who adopted his suggestion of distilling cheap brandy from wine fortified with extra sugar. Henry struggled to reconcile working with the production of alcohol, having pledged to “not only abstain from the use of alcoholic drinks, but to discountenance their use and manufacturing.” In an attempt at reconciliation, he would later in life pen a “sincere and convincing apologia pro sua vita.”

In 1873, Booth became interested in the Reformed Episcopal Church movement. Henry’s association with this movement would initiate a lifelong partnership and friendship with Frederick Woolfenden, Postmaster of Detroit and eventual Deacon of Detroit’s Reformed Episcopal Church, and James E. Scripps, Publisher of the Detroit Evening News. Through the support and urging of these men, the Booths would settle in the city of Detroit permanently by 1882.

Booth was also an inventor and received a United States patents commission during the years 1875-1887. His inventions included Ka-O-Ka (a coffee substitute) and a ventilated coffin. At the same time, Booth was a prolific writer and speaker. His articles were published in the Detroit News as a religious page called "Peregrinations of a Church Tramp" and he spoke at many Detroit area churches. Out of this experience came his unsuccessful attempt to revive the practice of family prayer through the "Bell, Book and Candle Society."