Ossining Tutors

About Ossining

Ossining, New York is a town that consists of two villages, Ossining Village and a part of Briarcliff Manor (the other part of Briarcliff Manor is in the town of Mount Pleasant). Within Ossining is the gravesite of one of New York and Connecticut's most intriguing residents.

The Leatherman was a vagabond that became famous because of his apparel. He wore clothes, a hat, scarf, and shoes all made from handmade leather. The Leatherman traveled a circular route between the Connecticut River and the Hudson River. He was known to have traveled this route from 1857 to 1889. Although very little is known about the Leatherman’s true identity; it is believed that he was French-Canadian. He was fluent in French, and at the time of his death, a French-language prayer book was found among his possessions. He spoke a small amount of broken english, but when he communicated, it was typically through grunts and hand gestures. When asked about his background, he would stop talking. It was also believed that he was Roman Catholic because on Fridays, he would decline meat.

The Leatherman walked a 365 mile route that he repeated every year. He would walk from town to town, staying in one spot for only about 34 to 36 days. The Leatherman lived in rock shelters that were nicknamed “leatherman caves.” He would go into town every five weeks or so, to get food and supplies. While people are not sure how he made money, he did go to stores to order what he needed. One store kept a record of his order which was; “one loaf of bread, a can of sardines, one-pound of fancy crackers, a pie, two quarts of coffee, one fill of brandy and a bottle of beer.” People would also give him food and because his route was so consistent, they often had food ready for him, which he ate on their doorsteps. Ten of the towns that the Leatherman frequented, even passed ordinances that made him exempt from the 1879 “tramp law”. The Leatherman could have tutored others in how to successfully live the life of a nomad.

At one point, the Leatherman was arrested and hospitalized. After his hospitalization, it was decided that he was “sane except for an emotional affliction.” Because he had money and wanted to be free, he was released from the hospital. The leatherman survived years in harsh east coast conditions, but was able to survive because of well-built rock shelters and small fires to keep warm. When he passed away in 1889, it was due to cancer of the mouth, that is believed to have been caused by tobacco use. Today, his final resting place is in Ossining, New York and his headstone simply reads, “The Leatherman.”

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