Big Indian Wilderness — Catskill Mountains

Big Indian’s “Story”

Lately, I am becoming more and more interested in the history behind the mountains we climb and the towns that we visit. Until now, I have thought very little about what history contributes to my ability to enjoy this hobby the way that I do. In the past I have found value in the challenge of a mountain, the presence of mind required by (or made possible by) the outside world, and the uncertainty of what will present itself around each new bend in the trail, but it has been all together self-serving. I have thought mainly of what the trail is for me and hardly at all about what the trail has been for others.

As Kyle and I made our way to Big Indian Mountain, he turned to me and said, “Big Indian is named after a Native American named Winnisook. He was really tall, I guess.”

“Wait…so the mountain is literally named “Big Indian” after a…big Indian? Isn’t that kind of offensive?” I said.

“Wow…yea…couldn’t they just have named the mountain Winnisook Mountain?” Kyle responded. Hmmmm.

When I got home I had to find a little more about the story myself.
What I found was pretty interesting. 

At one time, the Catskill Indians inhabited the area just north of Esopus creek. Winnisook was a 7 ft tall Catskill Indian who fell in love with Gertrude Molyneux (a white settler of the area) and asked for her hand in marriage. Her father had “objections” and said “absolutely not.” Gertrude was then promised to a white man named Joseph Bundy who turned out to be a real jerk. Gertrude wasn’t having it so she ran away with Winnisook and eloped. They were a runaway couple in the mountains and they started a family of their own. Basically, Gertrude was a real BA.

Rumor says that Winnisook was stealing cattle and the farmer spotted him. Bundy led a party of his bros to find him. They chased him to the top of the mountain we now know as “Big Indian,” shot him with a rifle and Winnisook died.

The website where I found this story calls it a “myth.” Considering the ways that stories travel in American history, it would be impossible to know what actually happened. The fact that it stands as a “rumor” is super interesting and slightly disturbing all on its own.

Quick Details:

Range: Big Indian 
Elevation Gain: 
~3,350 ft.
Peaks: Balsam, Haynes, Eagle and Big Indian
Difficulty: Easy-Moderate
Date: Nov. 17-19, 2017
Temps: ~25-45℉
Elevation: ~3350
(W) Friday Night: Clear skies, Mid-Upper 20s
(W) Saturday: High Winds, light-heavy rain in the evening, Low 30s
(W) Sunday: Rain giving way to sleet, Low 30s
Conditions: A light dusting of snow above 2500 ft.
Trail Head: McKinley Hollow

Marked Map - Big Indian

The Hike:

We started our hike on Friday evening at the McKinley Hollow parking area/trail head. We followed the red trail .75 miles to the McKinley Hollow shelter where we spent the night.


From the shelter, we hiked up the biggest incline of the weekend on the Oliveria Mapledale trail (Red) until it intersects with the Pine Hill West Branch trail (Blue). We turned right on the blue trail to head up Balsam Mountain. Just past the peak of Balsam there is an excellent view. It would be our only view of the weekend so we went for it (obviously).


Retracing our steps we hiked back to the the junction but continued straight on the blue trail rather than following the red trail back to the car. The blue trail takes you straight past the cairn that marked the top of Haynes Mountain. Another 1.4 miles of easy ridge walking took us to a short turn off to Eagle Mountain (turn right). The trail to the peak of Eagle is not marked, but it is clearly defined.


From the top of Eagle, it’s a 2.35 mile walk to the turnoff for Big Indian Mountain. The final quarter mile is untrailed but simple. The fog caved in on us as we followed our footsteps back to the trail and started to make our way back towards Eagle and Haynes Mountain.



At the junction we turned right. There are flat spots perfect for camping on either side of the trail. The flat areas to the left hosted a ton of downed trees, and a few limbs were hanging inconspicuously from their rotting trunks. The forecast called for heavy rain and wind–no thanks, I’d rather not be crushed by a tree. The right side was much cleaner and had some healthy looking trees so we called it good over there.


It rained HARD all night long (accumulation of more than an inch). On a night like this when it doesn’t let up and the fog lays down heavy around you, there’s no escaping the condensation inside a single wall tent. Everything was wet. Luckily we stayed dry inside our sleeping bags and in the morning all we had to do is pack up and hike out!

The Mitteneer’s Rating

  • Group Rating (1-20): 15

The hike from the McKinley Hollow shelter to the intersection was the only steep part of the weekend. It took ~30 minutes and then it was over. This could be a good or bad thing depending on who you are, but we typically like a challenge. In comparison to other Catskill hikes it was pretty uneventful. Hardly any climbing involved and only 1 view.

What we liked: 

  • The fog came down fast and thick at around 2 pm on Saturday. It was beautiful in the dense conifer forest located above ~3400 feet.
  • The initial climb up the hollow was beautiful and slightly challenging.
  • After the first climb, the hike was a relaxing ridge walk with a ton of beautiful trees, lots of lichen and moss, and just a tiny bit of snow. Can’t complain about that!

Big Indian Mountain has several approaches and we didn’t hit every mountain in this wilderness, but I liked the way we took on this area for the first time. Check out the links below to see how other people approach these mountains.

Until next time!

Sincerely Yours,
The Mitteneers


  1. More on THE Big Indian, Mr. Winnisook
  2. The 3500 Club on Big Indian
  3. The Big Indian Wilderness from The New York State Department of Environmental Conservation
  4. ALL the Approaches from the Central New York Hiking Website
  5. Day Hiking and other options from the REI Hiking Project Website

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