The aim of this blog is to bring together into one place the locations of all of the Old Leatherman Caves in CT and NY so that you can visit them yourself or learn more. It will be an ongoing project so there will be sections with ‘no current information’ which I plan to complete throughout 2020 and beyond. Each entry will give you information, a little history and pictures and description of how to find them to visit them yourself

The caves are in ‘loop order’ starting with where he died and moving clockwise round his 365 mile loop in order. This is the same route and order I did my 9 day Fastest Known Time in 2019.

Who Was The Old Leatherman of Connecticut?

In 1883 in Connecticut in the USA a man appeared with startling regularity between 41 towns in a loop that spanned 365 miles. Every 34 days he would appear at the same town. He did this for 6 years before dying on the 20th March 1889. He had first been seen in 1857 and in the earlier parts of his life was reported wandering as far north as Vermont and Canada.

He is known simply as ‘The Leather Man‘

THE HISTORY OF THE LEATHERMAN

Newspaper articles described the man as wearing a hand made leather suit ( hence his name) carrying a heavy bag and being seen to sleep in a series of caves on the route which he carefully looked after.

”Sane Except for an Emotional Affliction with a remarkable appetite”

The man and his trail defined him but ultimately killed him. We do not know his name, nor any backstory and so he has become a phantom on a trail that was slowly lost as towns expanded and roads were built in the coming years. Like himself, the information online is sparse but a superb book ‘The Old Leather Man’ by Dan W Deluca provides a collection of information about him without drawing any conclusions. Its the most honest, unbiased historical account I’ve read.

So here in order are guides to most of the caves. This is a ‘working project’ so there is plenty of information still missing that I need to go find or put together here .

George Dell Farm Cave – New York – Where he died

Briarcliff Manor Shelter Cave

Located on Hillcrest Drive, about one hundred yards past the dead end sign, on the right, next to the road. This shelter is on the Old Ryder Farm near the Old Dell Farm where the Leatherman died.

Leatherman Cave – Tinkers Cave – Mt Kisco

On Private land on the Wood Family estate near Mt Kisco / Bedford Hills area. I was lucky enough to be invited to see the cave by Jim Wood.

Bedford Hills Cave – Bull’s Hill Cave

Location and finding Old Leatherman Cave Bedford Hills

This cave is situated on the corner of Cherry Road and Bedford Road in Bedford Hills. At that junction you will find a Gas Station that you can park in. Directly above the car park is a very steep cliff hill and about 2/3rds of the way up this hill you will see the small 4ft triangular cave entrance. This scramble is not for the feint hearted. My recommendation is to climb it to the right and start your ascent when you have the three windows in the roof of the building by the wall directly behind you. After a short scramble you will find a sort of path that runs parallel along to the left to get to the cave entrance.

The Old Leatherman Cave – Ward Pound Ridge – New York

The Ward Pound Ridge has a map with useful intersections on it.

These numbers are shown on the park map and referred to in the description below. Since the trail system in the park is complex, hikers should obtain a free park map before beginning the hike. This hike will generally follow the Red Trail, but with several detours to include a number of interesting features.

From the circle at the end of the road, bear right and follow a road blocked by a wooden gate. Just beyond, pass a kiosk on the right and come to a fork at intersection #70. Bear right, following the red and green arrows, then bear right again at the next intersection (#53), as one leg of the Green Trail leaves to the left.

Proceed ahead on the Red and Green Trails, passing intersection #54 on the right. At intersection #31, turn right onto the Leatherman’s Loop Trail (LL-on-white blazes). When you reach the next intersection (#26), proceed straight ahead, but turn left at the following T-intersection (#27) and  follow the “LL” blazes, which proceed along a winding route to the top of a hill.

Here, just to the right of the trail, rock ledges afford a panoramic west-facing view over the Cross River Reservoir. A wooden bench has been placed here, and this is a good point to rest and take a short break.

Continue ahead along the Leatherman’s Loop Trail, which descends rather steeply on a footpath. After passing under an overhanging rock, you’ll reach intersection #29. Turn around, and you’ll see a tree with arrows pointing in two directions and a sign “to junction marker 27.”

Bear left at this tree and follow a white-blazed trail uphill to the cave.

The Lead singer of the Band Pearl Jam Eddie Vedder was once at Ward Pound Ridge and after hearing about the Old Leatherman wrote the song ‘Leatherman’

The Old Leatherman Cave Brewster

leathermans cave in brewster n.y. is peter and janes rock shelter. This rock shelter and others can be found in the book “Diary of an unknown archeologist’ Shelia Sabo  There is a photograph of the shelter in the book. 

The Old Leatherman Cave Turkey Mountain Yorktown

Turkey Mountain in Yorktown N.Y. is a public park. In Delucas book “the old leatherman” he mentions turkey hill as a site. There are several rock shelters to choose from on the mountain, all easily accessible from the trails there. I have not yet visited this area.

The Old Leatherman Cave- Ridgefield CT

At the Southern Tip of Seth Low Pierrepont State Park is Limestone Preserve. The Leatherman Rock Shelter is about 300 yds West of the centre of Taylors Pond and about equidistant between the Pond and Mimosa Circle Road.

I gained Access to the Limestone Preserve by parking at the end of Pinecrest Drive then walking into the woods to find the Orange/White blazes. From there you will cross a small footbridge where you turn left then follow the path for a few minutes. After that you will need to Bushwhack on a S/SE bearing to get to the cave which is 175 yards South West of the Southern end of Miller Pond. I strongly advise using a GPS unit. The Co Ordinates are 41 18.906’N 73 29.626’W . The cave is near the top of a very steep slope so you will need to take care.

A massive thankyou to Peter J Markey for helping me find this one.

Barnes Property Cave – North Woodbury

Near Dug Way . No more info currently.

Thomaston Watertown Leatherman Cave

This is located on the Matttatuck Trail through Black Rock State Park. The cave is at the peak next to Cranes Lookout and is located where the Mattatuck Trail meets the Jericho Trail. The Mattatuck Trail has blue blazes that lead directly through the cave and out the other side. Parking is at the Park off Route 6. Its a 2 mile hike out and back that’s tricky and steep and not recommended in bad weather. I also have a suspicion based on older books and guides that there is a ‘real ‘ leatherman cave further down the slope and closer to water that he is more likely to have used than this one. I’ve now been there twice and need to go one last time to be sure.

Harwinton Cave – The Old Leatherman

This cave is near Junction of Hill Rd and route 118, just overlooking a crescent shaped pond. With two separate newspaper articles from the period describing its location and its proximity to water and being on the route I mapped out its certainly one of his genuine haunts.

A local to the area called Brian was kind enough to take me out to this cave which he had discovered in the last few years. The cave now sits on private property so isn’t accessible from the road anymore so I wont be posting its exact location.

We took a row boat (!) to go see it. It sits with a significant overhang and was likely to have had wood piled up across the front when he used to use it.

Torys Den – Leatherman Cave

This cave was also used by the Tories in Revolutionary Times as a hiding place. It is located on the Tunxis Trail with closest access via East Plymouth road off Route 72.

Location

Secret Leatherman Cave near Tories Den

This cave is about half a kilometer from the Torys Den area and in my opinion far more likely to be his actual cave due to its proximity to water and being away from areas people at the time knew about. There is no path to or from this cave currently.

Leatherman Cave Southington – YMCA Camp Slopers Pond

This Cave is located on the Green Blaze Trail within the YMCA camp at Slopers Pond. As this is technically on private land you may need permission to visit this site.

I was lucky enough to get access to this cave as it was on the path of the course for the CT Trailmixers Spring Fling Race while I was there.

There isnt a lot known about this particular shelter except that the Old Leatherman had piled up old railway sleepers across the front of it to improve it as a shelter.

To find it simply follow the Green Trail round Slopers Pond and it is shortly after where the purple trail disects the green trail and just past two small wooden bridges to your right hand side. You cant miss it because of the Old Leatherman Cave sign on the path itself.

Meriden Hubbard Park Cave

Follow the path to the bridge going over 691 and up the hill to a wooden bridge on the left. Go over the bridge and up the hill to a stone bee hive spring. Taking a left and follow the path , staying to your right. Just below the base of the radio tower near the base of the cliff you will see his cave.

Meriden – Mount Higby

Located north of Preston Notch on the east side of Mount Higby, near the old plane crash. It tool Brian and I some time to find it but the exact location is at 41 33.104′ N 72 44.349’W.

The cave is only about a 1 minute walk from the site of a plane crash that happened in 1954. You can still see signs of the wreckage there.

Leatherman Cave Westbrook Pequot Park – Elijah’s Ledges – Lays’s Ledges

This Cave is on private Property in Pequot Park in Westbrook.. I was lucky enough to get kind permission from Leighton Lee who represents the company that are now the new owners of the land this cave is on.

Leatherman Cave Clinton CT

This cave is on the west end of Clinton. It is off of Nod Place to the south and it’s just north of the railroad tracks. Be careful in your travel planning as there are several “Nod” roads in Clinton. The cave was rediscovered in 1979 according to the book “History Repeated” by Beatram Smith. Look for the far right corner of the car park in the industrial area and then the cave is just over the ledge beyond it.

This small cave is about 4 feet wide at the mouth, 8 feet deep and unless you are very tall, you can stand up in it at the back end. There is a cleft at the ceiling that would allow smoke from a fire to escape. There is a big beech tree just in front of the entrance that has many initials carved in it. Bring a flashlight to get a good look inside the cave.

The “hike” to the cave will not be the most pristine on the loop, as the cave is only about 500 feet from the road. The cave is in a wooded section bounded by Nod Place, Nod Road and the railroad tracks.

Old Leatherman Cave Guilford Jacobs Lane

The cave is located on Water Street near where it meets Jacobs lane, directly opposite a house on the main road. The story is he used to sit in this shelter and wait for the family opposite to feed him.

Old Leatherman Cave Westwoods near Guilford

This cave is located on the green trail on their Preserve Map. On the map its marked at location 21.

There is a link to the map here

The Old Leatherman Cave Hamden – Fann’s Shelter

Owned by Hamden historical society . Located off Joyce Road in Hamden . I plan to find/ visit this soon.

Leatherman Cave – East Haven – Totoket Cave

How to find the cave

This may be one of the hardest caves to visit. At the moment you need to park next to the public basketball park on Rock Road in East Haven. From there you need to go up the very steep ridge which has nothing really in the way of a path. At the top you will find an unmapped red triangle blazed path which you turn right on and walk for about 2 to 3 mins. From there you are looking on your left for a small v groove gorge with a wet stream area through it about 20 to 30 m from the path. the exact dropped pin location is 41 18.940N and 72 50.298W . It lines up with Cecilia drive to the north and is equidistant between the lake itself and Rock street.

One of young Rodgers ( who lived in Branford and followed the Leatherman) photos was taken after he followed Leatherman to his next stop, a cave in East Haven near Eagle Crest above. It was called his Totoket cave after the Indian name for the area. It was described as overlooking Saltonstall Lake and is difficult to find.

Old Leatherman Cave – Wilton CT

A local to the Glen Hill Lane area of Wilton called Perry has known that a leatherman cave was on private property there since his childhood. The cave is not accessible to the public and sits near a stream.

Initially the Old Leatherman had a shelter overhang located on an outcrop that now is the shore of Rock Lake in Wilton. This is only accessible during the summer months.

As time went on and this area became more flooded The Old Leatherman located found a new cave overhang further to the South on what is now private property surrounded by beautiful overlooks and a waterfall cascade leading down to the reservoir.

Old Leatherman Cave – New Canaan CT

This cave is now on private undeveloped land. It is south of the end of Parish Lane and located off Weed Street just south of the junction of Ash Tree Lane. If you cross a small stream with a large old ornamental lake the cave/ shelter is high up to the left of the cliff face near to the border with the next property on the left . As this is private lane you will need owners permission to visit this cave.

Leatherman cave bear rock shelter

1857 long ridge road 06903 private house. I plan to ask for permission and hope to see it at some point.

The Old Leatherman Cave Greenwich Aubadon NY

This is located within the Audabon Preserve. This is a bird sanctuary and the cave is not on a main trail. I was lucky enough to be shown its location but cannot disclose its exact location to protect the wildlife and park rules.

The Old Leatherman Cave Armonk NY – Herlickers Cave

This cave is located on a ridge at the back of an Industrial Estate in Armonk. It is adjacent but not in the Betsy Sluder Nature Preserve. Look for Leatherman ct on the map and the ridge it is in is located inbetween Leatherman Ct and the H Weiss Building. You will need to be on the west side of Bear Gutter Creek. Best access is from the Labriola ct road. Once ‘in the bush’ look upwards for the steep ridge and the cave is roughly half way up the ridge. Its unclear if this is private or public land. The cave overlooks the Corporate Librarian Building next to H Weiss.

Triangulating the location on a map with nearby landmarks puts the cave at 41 07.05′ N and 73 43.39′ W.

Cave Shelter – Byram River Gorge – Greenwich

no current info

Other potential caves with no information

Leatherman’s Cave – Bridgewater

Leatherman’s – Blen’s St. – East Bristol

Leatherman’s – Chester –

note from nearby resident – Old Leatherman’s Cave in Chester. It is a 40-minute fast hike north of Deep Hollow Road in Cockaponsett State Forest. It’s just east of one of the sections of the old town road that ran between Chester and the Tylerville section of Haddam. The cave is west of the power lines and south of the Route 82 connector from Route 9. On the USGS Deep River 7.5-minute topographic map, it’s located right next to the last T in Forest. It’s close to the source of Deep Hollow Brook, which flows north into Roaring Brook.
It’s a textbook cave for him with a large rock in the center for heating. He carved out a section of softer stone on one side of the cave in the ledge to make a cabinet for himself.

Leatherman’s – Joe’s Hill – Rt. 84 – Danbury

Leatherman’s – Durham – Bear rock on Mattabesset ?

Leatherman’s – Pine Rock Shelter – East Haven

Leatherman’s – Holt Hill District – Plymouth

Leatherman’s – Essex

Leatherman’s – Prospect Mt. – Litchfield

Leatherman’s – Iverton

Leatherman’s – State Park- Meriden

Leatherman’s – New Fairfield

Leatherman’s – New Milford

Leatherman’s – Norwalk

Leatherman’s – Saybrook

Leatherman’s – Westport – On the borders of Essex, Westbrook and Old Saybrook there is a cave that according to family lore is a Leatherman cave. If you’re interested, its near what is now Brittney Lane off of Rt 153. My family lived on that property for a long time before it was developed. My recollection is its in the woods closer to 153 on the south side of Brittney lane (on the north side there is a small pond). I

Leatherman’s – Rimond Rd & Fountain St. – Woodbridge

Leatherman’s – (4) – one at Dugway – Rt. 6 – Woodbury

Leetes Island Caves – Guilford

This page was also recently mentioned in a great article by Forbes here.