Looking for a scenic hike in Connecticut with an interesting story behind it? This is a great option! In 1860, a mysterious man nicknamed Leatherman appeared in the Watertown, Connecticut area. He wore a jacket covered in leather patches and walked from Connecticut to central New York (360 miles) in about a month. His true identity was lost to history, but he often took refuge in various caves in the area. One small cave in Watertown where he was rumored to have slept now bears his name. You can access it with a challenging trail from Black Rock State Park.

Little is known about Leatherman, and rumors surround his life. He passed away in 1889 in a New York cave. No one knows why he walked so much.
Jaclyn Martorelli/Google Maps
Many Connecticut natives have stories of their grandparents leaving food out for the Leatherman as he traveled through their town.
The trail that leads to the cave bearing his name can be accessed from Black Rock State Park: just walk east along the Mattatuck Trail. You'll need to take a sharp left turn at the Jericho Trail sign.
Kat S/Google Maps
There are quite a few steep areas and rocky scrambles. This is definitely not an accessible trail and it's probably not the best option to bring young kids or dogs.
Amy Webb/Alltrails

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The cave is small and was formed when rocks fell down onto one another. As you walk through, make sure to think about the poor Leatherman out on his lonely journey.
Steven Hopkinson/Alltrails
Some of the overlooks from the trail are absolutely gorgeous. Connecticut is such a lovely state!
Morgan Vallee/Alltrails
The trail ends right on top of the cave.
David Goldstein/Alltrails
The hike is 2.2 miles each way: it's an out and back trail. Make sure you wear appropriate footwear and watch your step at all times!
chad nimons/Alltrails

This is a unique hike in Connecticut with some history behind it. Check it out next time you’re in the area!

For more information about the Leatherman Cave Trail, check out Alltrails.

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Black Rock State Park, 2065 Thomaston Rd, Watertown, CT 06795, USA