The Old Leatherman's Cave

The Old Leatherman is a legend of Connecticut lore, whose presence in the Nutmeg State was first noted just prior to the Civil War. Little is known about who he was, how or why he came to Connecticut, or his nomadic existence. It is believed that, despite the attention he drew to himself, he spent little if any time socializing with those he encountered in his travels through Connecticut and New York. Still, his legend persists.

From the time he first appeared in the area until his death in 1889, the Leatherman’s sole pursuit seemed to be walking a 365-mile, 34-day circuit through southwestern Connecticut, spilling over slightly into lower New York State. The trips took him through towns including Danbury, New Fairfield, Watertown, Middletown, and New Canaan, into Westchester County, New York, before circling back to Danbury.

His moniker reflected his attire: clothed head to toe in a stitched, heavily patched leather suit. He subsisted on the generosity of townspeople and farmers who came to know him, some offering accommodations in their homes or barns. The timing of his recurring trek was so consistent that locals, anticipating his arrival, would often leave food waiting for him. But despite this hospitality, his preferred form of shelter seems to have been caves. Of these, three are confirmed with a possible fourth in Middletown, Connecticut.

A fine example of where he would hole up for the night can be seen firsthand by following hiking trails in Black Rock State Park, Watertown, Connecticut. The Old Leatherman Cave in Watertown is a talus cave, formed from empty spaces between fallen boulders (also known as a boulder cave). Talus caves are a type of “pseudokarst,” created by mechanical processes rather than the dissolution of bedrock or limestone. This particular example is large enough to fit several people and is still worth a visit today.