Leatherman's Cave

This talus cave — a shelter formed in the gaps between fallen boulders rather than carved by water — sits along the Mattatuck Trail and is known locally as the Rock House. Local tradition has long connected it to Connecticut's "Old Leatherman," a vagabond who walked a repeating 365-mile loop between the Connecticut and Hudson Rivers from roughly 1857 until his death in 1889, resting in caves along his route. That specific connection to this cave isn't actually documented — the earliest known reference linking it to him is a 1920s Boy Scout hiking account, three decades after he died — but the name has stuck, and it's said to still be haunted by him.