Hike Report: Indian Head Wilderness–Catskill Mountains

Quick Details:

Trail(s): Overlook Spur Trail, Overlook Trail, The Devils Path, Jimmy Dolan Notch Trail
Elevation Gain: 
~3,580 ft.
Distance: 18 miles
Peaks: Overlook and Indian Head
Difficulty: Moderate
Date: Nov. 24-25, 2017
Temps: ~26-50℉
Weather: Clear, sunny skies on Friday / Partly Cloudy on Saturday
Conditions: Small patches of ice and mud
Trail Head: Meads Rd.

Indian Head Wilderness

The Hike:

When we pulled up to the Meads Rd. trail head it was completely packed. The Buddhist Monastery that sits adjacent the trail head is apparently a really popular tourist destination. According to the park ranger monitoring the trail head “it’s like this seven days a week, 365 days a year.” If you’re planning to head up the Overlook Mountain Spur Trail, arrive early or be prepared to park a 1/2 mile down the road (that’s what we did).

The Overlook Spur Trail is an old forest road and it’s steep. Many people (there was ~100 people with us) take the Spur Trail up to the fire tower on the top of Overlook mountain (2.4 miles one way). You are nearing the top when you encounter the ruins of the “Overlook Mountain House,” a hotel that burnt down…twice! In 1875, the hotel burnt down, they rebuilt the hotel just for it to burn down again in 1921. As you explore, check out the charred pieces of wood in the window frames.


Continue following the Red trail to the Overlook Fire Tower. In warmer weather, there is a small museum with some interesting pictures and information about the Overlook Mountain house in its “hay day.” There is also another view 100 yards behind the mountain “museum.”

For us, the real hike started once we started the Overlook Trail. As we made our way down from the fire tower, we turned right on the blue trail and hiked a peaceful 3.7 miles past the Devil’s Kitchen Shelter to our “secret campsite.” On the way, make sure to stop at Cod Fish Point. Kyle heard a woman reading about Cod Fish Point out of guide book once–he heard her say, “a bunch of quarry workers got stranded at this overlook and all they had to eat was canned cod fish.” Who knows if that’s true or not, but we laugh about it whenever we’re here.

Our secret campsite and Kyle’s expert tarping skills

In the morning, we got an early start for a straight forward hike. We followed the red trail (The Devil’s Path) up and over Indian Head Mountain. The trail leading up Indian Head is steep, but it’s beautiful all year round. This is the highlight of the loop–I recommend taking your time. At the junction on the other side of Indian Head, we turned right onto the Jimmy Dolan Notch trail (Blue) and right again to return to the Devil’s Path (Red). The Jimmy Dolan Notch trail is a straight forward descent that starts out steeply and levels out after about 1/2 mile. After turning right onto the red trail, you’ll climb a few hundred feet as you make your way back to the Devil’s kitchen lean-to.

Sherman’s Lookout
Sherman’s Lookout
We call Kyle the Moss Boss–he’s also always giving the mini trees some love. 
Bonus view just past Sherman’s Lookout
Turn Left at the junction between Indian Head and Twin for the Jimmy Dolan Notch view


The Mitteneer’s Review:

  • Thumbs up: The entire Indian Head Loop is amazing.
    • We loved the hike up Indian Head. It’s a relatively steep climb at 1347+ feet over 2.25 miles. If you’re not an avid hiker, just go slow!
    • A few of the climbs are sort of tricky. At the most difficult, you’ll climb ~15 ft. relying on tree roots as holds. I’ve read a few reports that caution hikers against this section, but I’ve climbed this mountain 5 times and I’ve seen all sorts of people make it up (young and old)–it’s definitely doable.
    • There are three really nice views on this mountain: Sherman’s Lookout, one just shy of the top (nameless), and Jimmy Dolan’s notch (left at the junction).
    • The top of Indian Head doesn’t have a view, but it smells like Christmas Trees, it’s full of moss, and it’s a little cold and windy–Just wonderful.
  • Thumbs Down:
    • The trail population up Overlook Mountain is dense. It is highly trafficked by a wide variety of folks. We’re cool with sharing the trail, but this was a CROWD. Make sure you’re ready to share your experience with ALL the tourists and plan to keep going if you’d like a more secluded experience.
    • The hike to Overlook Mountain is steep (which we like), but there’s not much to it. I’d call it a quadruple track. Like I said, to get into the nature you’ve got to get past the fire tower.



Further Reading:

  1. Overlook Spur Trail from the REI Hiking Project
  2. More on the Overlook Mountain House 
  3. Overlook Mountain Wild Forest from all angles from the NY Department of Environmental Conservation.
  4. Indian Head from Catskill Mountaineer
  5. The Devil’s Path from the NY Times

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