The trip Leatherman Cave is an uphill hike over rocky cliffs to one of the caves where New England’s legendary Leatherman is said to have stopped on his endless travels throughout the state of Connecticut. This section of the Mattatuck Trail is located in a segment of state forest in Watertown, Connecticut with plentiful scenic outlooks. Hiking to the cave involves climbing and some bare, flat-rock exposures. Children or inexperienced hikers should use care when near cliff edges and when descending into Leatherman Cave, which has very steep drops.

Leatherman Cave is actually made up of several enormous rocks stacked together like a house of cards. One entrance is a tight fit, requiring visitors to crawl through an opening. The other side of the cave is totally open.

Leatherman Cave is a cool place in the summer as it is completely in the shade, lying as it does in the shadow of a mountain. In the center of the dark cave everything is very quiet and still.