Henry W. Bennett was the youngest son of Benjamin L. Bennett and Margaretta (Hall) Bennett. He was born in Rutherford County, Tennessee, and was likely named after his maternal uncle, Henry Hall. Henry's father, Benjamin, had three children from a previous marriage, Anne, Thomas J., and Martha.
Henry's father Benjamin was a well established farmer in the 1850's, with over 300 acres in cotton and several town lots in nearby Warrenton. Benjamin died of rheumatic fever in the spring of 1860, when Henry was four years old. Henry continued living on the plantation with his mother, older brother John S., and half sister Martha. His maternal uncle, Henry Hall, was a bachelor who lived nearby and helped them run the estate.
In the mid 1870's Henry began working in the Guntersville mercantile business.
In 1881 Henry was named postmaster of Guntersville, and was described as "courteous" and "efficient" by the newspaper. Henry's maternal uncle, Henry Hall, worked as deputy postmaster.
Henry married Mary E. "Bettie" Hunter, daughter of Rev S.B. Hunter, May 1, 1883 at Guntersville. The paper called him one of the town's most promising young businessmen. The couple had a son, Benjamin, in August 1885. Henry's brother John S. became Sheriff of Marshall county around this time.
Henry's health had begun to decline shortly after his marriage, according to the newspaper, and by the summer of 1885 he was forced to retire from work. He died at Warrenton in February 14th, 1886, age 29, and was laid to rest in Bennett cemetery with his parents. The illness or condition that caused his death is unknown.
Henry and Mary's infant son Benjamin died on May 4th, 1886, and was laid to rest in the Bennett cemetery with his father. Little Benjamin, named after his grandfather, was only 9 months old.
Henry's widow, Bettie, remarried to Dr. Thomas S. May, son of Judge W. May, in 1888. In April 1889 this couple had a son, Tommy, who also died young, at the age of two.
Since Henry died without heirs, the bulk of his father Benjamin's remaining estate went to his brother, Sheriff John S. Bennett, and subsequently to John's sons, John May and Gus.
(information from Nashville Christian Advocate, March 1886, Guntersville Democrat, and Marshall County marriages, US Census records, Marshall county probate records for Benjamin Bennett)