Henry Hill grew up in Catskill, N.Y., where his father, Richard (1763-1846) had a ship-building business and a store. Henry started his career in commerce at the age of thirteen, beginning with a clerkship at his cousin Hiland Hill Jr.'s store. One year later, in 1809, he decided to discontinue his education in favor of another clerkship, leaving home for New York City in the process.
Between 1815 and 1816, Hill went to Europe on a combined commercial buying and pleasure trip. Soon after he returned home, he was chosen as an agent for the merchants, Palmer & Hamilton in Chile, with the promise of becoming a partner in the future. He remained with that firm for several years before returning home, marrying, and starting a family.
Hill had been acquainted with his future wife (whose surname was probably Porter) since childhood, as her father had been the family's minister. Hill remarked that although there never was a formal engagement, "it seemed to be understood" that their "fortunes were to be linked," adding "she had always been my choice and we were good friends." The two married in about 1823 and settled in Boston (Dorchester), Mass. They had five children, only three of whom survived to adulthood.
Religion had an extremely important influence on Hill throughout his life. He faithfully attended church wherever he was and often sought comfort and inspiration in Biblical proverbs. In 1812, when Hill's mother, Sarah (Carpenter), died of "apoplexy" at age 49, Henry was grief-stricken, but found enough solace in the Bible to comment that his mother's death was "of spiritual benefit" to him. He abstained from both smoking and drinking, most likely for moral reasons. He was chosen as deacon of Park Street Church, a Congregational church in Boston in 1825. In 1850, he became deacon of Eliot Church in Roxbury, Mass., thus continuing his abiding commitment to religion.