A LITTLE LOCAL HISTORY: The Old Leather Man

One of the best-known American short stories is Washington Irving’s “The Legend of Sleepy Hollow”, which is set in the countryside around Tarrytown (Irving’s home Sunnyside is still there).

By Paul Hicks

One of the best-known American short stories is Washington Irving’s “The Legend of Sleepy Hollow”, which is set in the countryside around Tarrytown (Irving’s home Sunnyside is still there). Its tale of a headless horseman is said to have been based on folklore about a Hessian soldier, whose decapitated body was found after the Battle of White Plains in 1776. Irving’s story became such a popular legend that the residents of the Village of North Tarrytown decided to change its name officially to Sleepy Hollow in 1996.

Another legend, which involves Rye, Harrison, and other Westchester communities, is far less well known than the headless horseman. It is the curious story of a real person, known as the Old Leather Man, who regularly traveled on foot through parts of Connecticut and Westchester in the late nineteenth century. As Allison Albee, a former Rye resident and Westchester County historian, wrote in 1937: “Occasionally, legend and reality unite in the form of some remarkable soul who, through peculiarity or chance, assumes a role resembling the mythical characters we read about in childhood’s fairy tales. The Leather Man was one of these.”

Like the legendary Johnny Appleseed (who was, in fact an itinerant nurseryman named John Chapman), the Old Leather Man was a vagabond, wandering from place to place without a settled home or job. Since his death in 1889, several historians have uncovered bits of information about him, which have been collected and edited by Dan W. Deluca in “The Old Leather Man: Historical Accounts of a Connecticut and New York Legend”, published in 2008 by Wesleyan University Press.

According to Deluca, the first reported appearance of “Old Leathery” was in 1856, and from then until 1882 he traveled periodically between the Connecticut and Hudson rivers. Then, in 1883, he started traveling a clockwise circuit, following a regular route of 365 miles every 34 days until his death. Along the way, he lived rough, sleeping in caves, huts, and other shelters with only his all-leather outfit as protection from the elements. He made his clothing and his large bag by sewing together the tops of discarded boots.

A letter to the editor of the Port Chester Journal on February 10, 1870 stated: “I suppose that many of the readers of your valuable paper have heard of ‘the old leather man,’ who has for the last year or so been seen occasionally wandering around this and other neighborhoods, and who has established his winter quarters in a wood belonging to Mr. Joseph Park, and bordering the road running to White Plains, between Purchase and North Street.”

Joseph Park, head of the firm of Park and Tilford in New York City, lived in Rye in what is known as Whitby Castle (Rye Golf Club) and owned more than 2,000 acres of land in Rye and Harrison. When a large part of that land was sold in 1909 by one of his sons to a syndicate that formed the Westchester Country Club, the New York Times described the boundaries of the property as “running south of the Polly Park Road to North Street with Purchase Street cutting through it.” Therefore, it appears that the Old Leather Man’s local shelter was somewhere along Polly Park Road.

Another letter to the Journal, published on February 17, 1870, denied a report that Mr. Park (one of Rye’s leading benefactors) planned to eject the Old Leather Man from his property, commenting that the mystery man “has always been civil and quiet in his manner.” When he passed through the area in 1877, the Journal noted that, “Nobody knows who he is, where he comes from, what his nationality is, or what is his name and age.” The absence of information led to much speculation and an often-repeated tale of his being a Frenchman, who had immigrated to America after being jilted by his ladylove.

In a recent telephone conversation, Dan Deluca told me a story about a boot that was found at the Old Leather Man’s shelter in Mr. Park’s woods. It was discovered by Edward Clark who was born in Rye in 1862 and loved to hunt and trap as a boy. In later life he lived in Mamaroneck and practiced medicine. His son, Edward, was also an outdoorsman, who opened a tourist destination in the White Mountain Region of New Hampshire called Clark’s Trading Post in 1928. Among its many attractions is a museum where the Old Leather Man’s boot is on display.

After surviving the blizzard of 1888, the wanderer’s health gradually deteriorated, and he died near Ossining in March 1889 inside a cave on a farm he had often visited. He was buried in a pauper’s grave at the Sparta Cemetery, where a bronze plaque was unveiled at a ceremony in 1953. In 2011, however, his remains were exhumed and reburied in a more suitable location at the cemetery with the headstone reading simply, “The Leatherman.”
Anyone who is interested in learning more about this mysterious man should buy Dan Deluca’s book or borrow it through the Westchester Library System. Appendix C of the book gives useful information about “Selected Old Leather Man Sites Accessible to the Public.” Among the closest are a cave at the Audubon Greenwich Center in Greenwich and a shelter in Armonk. One of the best-known caves is at Ward Pound Ridge Reservation in Cross River. Information about the Old Leatherman and the cave is available at the Trailside Museum there and through their website at http://friendsoftrailside.org /index.html.