The Leatherman (ca. 1839–1889) was a particular vagabond, famous for his handmade leather suit of clothes, who traveled a circuit between the Connecticut River and the Hudson River, roughly from 1857 to 1889. Of unknown origin, he was thought to be French-Canadian, because of his fluency in the French language, his "broken English", and the French-language prayer book found on his person after his death. His identity remains unknown, and controversial. Indeed he predated the term hobo, some may call him the original hobo. He walked a 365-mile route year after year. His repeating route took him between towns arriving in a new town every 34–36 days in western Connecticut and eastern New York.
Living in rock shelters and "leatherman caves", as they are now locally known, he stopped at towns along his 365-mile loop about every five weeks for food and supplies. He was dubbed the "Leatherman" as his adornment of hat, scarf, clothes, and shoes were handmade leather.
Fluent in French, he communicated mostly with grunts and gestures, rarely using his broken English. When asked about his background, he would abruptly end the conversation. Upon his death, a French prayerbook was found among his possessions. He declined meat on Fridays, giving rise to speculation that he was Roman Catholic.
It is unknown how he earned money. One store kept a record of an order: "one loaf of bread, a can of sardines, one-pound of fancy crackers, a pie, two quarts of coffee, one gill of brandy and a bottle of beer".
Leatherman was popular in Connecticut. He was reliable in his rounds, and people would have food ready for him, which he often ate on their doorsteps. Ten towns along the Leatherman's route passed ordinances exempting him from the state "tramp law" passed in 1879.
The Leatherman survived blizzards and other foul weather by heating his rock shelters with fire. Indeed, while his face was reported to be frostbitten at times during the winter, by the time of his death he had not lost any fingers, unlike other tramps of the time and area. The Connecticut Humane Society had him arrested and hospitalized in 1888, which resulted in a diagnosis of "sane except for an emotional affliction" and release, as he had money and desired freedom. His ultimate demise was from cancer of the mouth due to tobacco use. His body was found on March 24, 1889 in his Saw Mill Woods cave on the farm of George Dell in the town of Mount Pleasant, New York near Ossining, New York.