Henry Hamilton Bennett was born in Farnham, Lower Canada on 15th January, 1843 but was raised in Brattleboro, Vermont. He later moved to Wisconsin in 1857 and got settled in Kilbourn City, today known as Wisconsin Dells. Here, Henry worked as a carpenter in the town. After the outbreak of the American Civil War, Bennett joined the army and fought in the Battle of Vicksburg before being severely wounded by the accidental discharge of his own gun. The tragedy prevented Bennett from returning to carpentry. This proved to be a blessing in disguise and in 1865 he bought a Kilbourn City photography studio, thus beginning his career as a photographer.

Because there was little demand for portraits in the area during that time, Bennett set his heart on landscape photography. The inspiration led him to build a portable darkroom and stock it with his camera and other necessary equipment with him across the local countryside taking pictures. He did not have to go far to find impressive scenery, for the Wisconsin River Dells, a gorge with numerous sandstone formations, was just outside Kilbourn City. Bennett loaded a boat with his photographic equipment and took many pictures of the Dells. Realizing that the three dimensional aspect of the rock formations would be lost in two-dimensional photographs, he began creating stereoscopic images that allowed viewers to see the Dells in three dimensions. Bennett made his first stereoscopic photo in 1868, which soon gained popularity and started being sold in many cities across the United States.

As people across the country started viewing more of Bennett's photographs of the Wisconsin Dells, they began to flock to Kilbourn City to see the rock formations in person. The area soon became a tourist destination for sightseers eager to leave behind the hustle-bustle of city life. Bennett capitalized on this, building the H. H. Bennett Studio in 1875 and using it to sell postcards and souvenir portraits to travelers. In the meantime, he continued to innovate in the field of photography by inventing a stop action shutter which allowed him to take photographs of instantaneous events. Previously, it took several minutes for a camera to take a picture, and any movement of the subject being photographed over this time caused the picture to become blurry.

After Bennett created the new shutter, he was able to take clear pictures of moving subjects. The best known photograph taken by Bennett with this device was an 1886 image of his son Ashley jumping between two rock formations in the Dells. Boston audiences of 1890 gasped when this photograph was projected as a magic lantern slide. Bennett also introduced narrative concepts, as noted by his great-granddaughter, Betsy Reese Grant, in The Bennett Story.

From 1832 - 1890, every spring saw raftsmen riding their lumber to market down the Wisconsin River. Bennett had always been interested in taking a series of pictures of their activities. In 1886 dry plates had finally become reliable enough that he did not need his portable darkroom. Henry and his son Ashley made a 100-mile, week-long trip on a lumber raft. Between Kilbourn and Boscobel, Wisconsin, he took 30 pictures of the raftsmen's activities and combined these with other pictures taken near Kilbourn and called the series, The Story of Raftsmen's Life on the Wisconsin. It was the first time a photographer wrote a ‘story’ with pictures, giving birth to Photo journalism.
Henry was also innovative in the way he printed pictures, building a revolving solar printing house that is now housed at the Smithsonian Institution. In addition, since early cameras were unable to accurately capture details of the sky or reflections in water after being adjusted for the light of a typical land photograph, Bennett wove together negatives from multiple photographs of land, sky and water before creating a final print. Bennett received much attention and appreciation for his advanced techniques, and was commissioned by the Chicago, Milwaukee & St. Paul Railroad to photograph the landscape along the company's track in Wisconsin. Bennett also took pictures outside the state, photographing an ice palace in St. Paul, Minnesota and the World's Columbian Exposition in Chicago, Illinois.

With portable film cameras becoming widespread in the 1890s, Bennett's career declined somewhat as tourists coming to see the Dells were able to take their own souvenir photos and no longer needed Bennett's postcards or portraits. Nevertheless, Bennett pressed on in his profession, selling gift shop type items from his studio to attract more customers and continuing as a professional landscape photographer until his death on 1st January, 1908. Following his death, Bennett's family took over the photography studio, remodeling it in 1917. His descendants continued to operate the studio until 1999, when the building was restored to its 1908 appearance and became a historic site operated by the Wisconsin Historical Society.

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