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Explore Watertown’s Famous Leatherman’s Cave

Leathermans Cave Watertown
Written by Nikki Pretter

If you’re from Connecticut, you’ve probably heard of the famous Leatherman. Here’s some history on this legend figure and his home in Watertown.

Connecticut is full of mysteries and stories that date back many years. Being so old, these stories often make it difficult to find the real truth. But regardless of the exact origins or details, Connecticut residents take pride in these myths. Leatherman’s Cave in Watertown is one of these stories that people love to tell.

The Leatherman

The infamous Leatherman was a wanderer who lived in Connecticut during the late 1800s. He received his name because of the fact that he was supposedly always dressed in a handmade outfit consisting of 60 pounds of leather.

The man walked in a 365-mile circle between the Connecticut and Hudson rivers, and he was said to have done this about 360 times over nearly 30 years. If you are from Connecticut you may have heard stories from your families about how they would give him their extra food. In addition to foodstuff, he would visit leather shops seeking scraps which he could then use to patch holes in his outfit.

This legendary figure stopped at a number of ledges and overhangs across the central and western portions of the state to sleep. No one truly knows why the Leatherman made these long trips, but there are a few different speculations. Some said that it was due to a lost love or broken heart.

Some gave him an identity as Jules Bourglay, the son of a woodcarver who loved the daughter of a leather merchant in Paris, only to have his advances rebuffed after he lost his fortune when the leather industry crashed.

Others declared that he was Rudolph Mossey, a French shoemaker whose wife ran off with another man to America. He followed her to the states, only to discover that she had died. Whatever the true tale is we will likely never know—he was unable to speak, so his identity is likely lost forever.

Though seemingly the stuff of nightmares (many stories say you could tell the Leatherman was coming by the smell of leather on the wind, or the creaking sound of his outfit as he approached), he was a gentle person. There are no records of him ever harming someone or stealing, and he was oddly loved by the people he visited, who would often send him on his way with an extra loaf of bread, tobacco, or coffee for his journeys.

He died in a cave in Mount Pleasant in 1889.

The Cave

The Leatherman Cave Trail is about 3 miles long round trip.  Located in Watertown, the trail is mostly used for hiking, walking, and nature seekers. Though it is called THE Leatherman’s Cave, there is evidence that this cave is just one of many that he called home as he made his 360-mile route through Connecticut and New York.

The cave is accessible along the Mattatuck Trail by hiking eastbound from Black Rock State Park or from Reynolds Bridge going west over the Naugatuck River. The hike will bring you to the top of Crane’s Lookout to begin, so you will be able to see some astounding views from the 780-foot-high peak which will allow you to put your imagination to work and feel as though you are able to understand what the mysterious Leatherman experienced on his trek.

The trail then goes down to the infamous cave, where if you choose to you can climb through a small opening in the ledge to make your way inside. The cavern was created when huge pieces of the rock ledge fell, ending up in positions that created a cave-like appearance. Although it not necessarily a true cave, the jumble of massive rocks under the ledge is still quite impressive.

It is best to access it April until November based on weather, the grounds conditions, and when the scenic nature aspects are in full bloom all around. The walk is primarily uphill so be ready to get a workout in for this adventure.

You can find a trail map of the Mattatuck Trail here, which may be helpful as you go out in search of the Leatherman’s Cave.

About the author

Nikki Pretter

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