Henry Hamilton Bennett was one of a handful of pioneering photographers of the 19th century. A contemporary of William Henry Jackson and Timothy O'Sullivan, Bennett eschewed the opportunity to photograph the vistas of the western United States for which Jackson and Sullivan are known, although he had the opportunity. He was invited to photograph the country's first national park, Yellowstone, but declined. Bennett's preferred subject was the Wisconsin River and the landscapes in the river valley near the city of Wisconsin Dells.

Bennett was born in 1843 in southern Ontario. His family moved to Vermont in 1844 and his father relocated the family again to south central Wisconsin when Bennett was 14. His interest in the new technology of photography was spawned by his uncle, George Houghton, who moved to Wisconsin with the Bennetts but eventually returned to Vermont, was a photographer.

Bennett, following his service in the Civil War during which he lost full use of his right hand, changed his vocation from carpentry to photography.