Indian Head & Twin (Sunset Hike)

Hiking Trail Description

This is my favorite hike in the Catskills. It has everything the Catskills can give you: classic Catskills forests, rugged terrain, excellent scrambles, and jaw-dropping scenic views.

Trailhead Parking

The parking area at the end of Prediger Road is a generous loop, with lots of space for cars, but this is a popular destination — on busy weekends you’ll need to arrive early to grab a spot.

BTW, between November 1 and April 15 every year, the eastern end of Platte Clove Road is closed. In which case you can use this alternate route to Platte Clove Road. It only takes a little bit longer.

Indian Head & Twin Hiking Trail

From the parking area, follow the red blazes of the Devil’s Path to the first junction at 0.2 miles. Do not turn right. That way is the Jimmy Dolan Notch trail which leads up to the col between Indian Head and Twin mountains.

Instead, keep straight and hike 1.45 extremely pleasant miles to the first of two junctions.

A very detailed description of the route up Indian Head can be found at Indian Head (Best Route). But here are the highlights from this hike.

About half way, you’ll pass over this sweet rock footbridge…

At the first junction, turn right.

At the second junction (which is only a few hundred feet farther on) again turn right and begin to hike uphill. It’s super lovely…

Lots of old trees, many of them first growth, populate this part of the mountain.

There are many old hemlock trees on the first part of this trail section, making up some first growth stands.

Sherman’s Lookout

About 3 miles into the hike, at around 3200’, you’ll pass Sherman’s Lookout on the left side of the trail. The view looks down across Platte Clove to Round Top and Kaaterskill High Peak.

The small lake you see below in Platte Clove is the lake that is fed by the rock-bridged drainage you crossed earlier.

You are now on Indian Head’s “chin”. Work your way around the chin.

At 3300’ an opening on the left side of the trail gives a framed view south to Cooper Lake, Ticetonyk Mountain and Ashokan High Point.

On the far side of the chin, the trail dips down into a small col below Indian Head’s “nose”. You will be confronted by a dramatic-looking rock chute about 80 ft in height. It may look daunting but take your time and you’ll figure it out. It’s one of the funnest climbs in the Catskills, and quite doable. (Turn back, here, if it feels sketchy to you.)

At the top of the rock chute is a wonderful view of Indian Head’s chin, with Overlook Mountain in the distance — the fire tower and radio mast are both visible if you look closely. This photo is from a little later in the year…

Beyond the nose, the trail dips down once more before the final climb to Indian Head’s summit. The trail up here is classic Catskills, so beautiful.

Indian Head Summit

A few hundred feet before the summit is another small scenic view, again on the left, looking south.

The summit of Indian Head is treed-in but it’s lovely and calm, a very special place on the mountain. The summit of Black Dome is similar in that it’s somehow, simultaneously, not much and a whole lot. Two of my favorite summits, and neither has a view.

Continue west. A few hundred feet west of the summit, you’ll have to climb down this tricky little rock chute. It’s not much but it always slows me down, and I feel like I need to climb down it very carefully.

On your descent toward Jimmy Dolan Notch, you’ll pass this boulder which I love dearly…

Jimmy Dolan Notch

Jimmy Dolan Notch is small and delightful, a great place to catch your breath and snack.

The Devil’s Path (red blazes) continues west. To your right, heading down, is the Jimmy Dolan Notch trail (blue blazes) you’ll be using later.

For now, continue west and begin to climb Twin Mountain. This part of the route (and Jimmy Dolan Notch itself) is covered in detail by Hike Twin Mountain via Jimmy Dolan Notch.

Conceivably, this rock formation has been in position since the end of the last ice age 13,000 years ago. It marks the entrance to the trickiest rock lift on this route. At the back of the rock scramble, a small handhold on the left side may help you lift yourself up — but watch your head. (A fuller description can be found in that other hike report.)

Above the rock scramble are several tricky sections, all of them so much fun to navigate.

At 3500’ I got a nice view looking back to Indian Head with the moon above…

Overlook Mountain with its two towers is also visible, again, from this spot.

Twin’s Lower Summit

Just a few minutes later, you’ll come out onto Twin’s incredible first summit. It’s lower than the true summit but has a much larger open ledge that offers an incredible view. Especially at sunset…

It can be quite windy up here, so make sure you have a few layers to throw on if you want to sit a while and take in the view.

The trail drops down below the viewing ledge, and continues west to the Twin’s true summit. The walking is easy and takes about 20 minutes.

Twin’s Upper Summit

It was getting dark by now so I don’t have photos from the summit. The view is good and there is a lot to see.

On the right, Sugarloaf is prominent and the western ridge of Plateau is also visible. Hunter Mountain’s summit can be seen in the distance. The long low mountain on the left is Olderbark. Behind Olderbark, 25 miles away, is the distinctive shape of Balsam Mountain. To the left of Balsam, you can see Eagle and Panther mountains.

Descent

To return to the lower summit and then Jimmy Dolan Notch, turn around and head back. Just make sure to take the left fork in the trail and head east. (The right fork continues on down the west side of Twin, heading onwards to Sugarloaf.)

This was one of my first night hikes. It was super fun. At this time of year, the night is not quiet. The air is full of strange nocturnal insects that glow when your lamp hits them.

I saw plenty of deer eyes in the woods around me, too. And there is a lot of activity on the forest floor: frogs, toads, and other critters.

I carry two headlamps on every hike. One for personal use, and a spare for back-up or in case someone else needs light. They’re so cheap now, and so light, and such great tools. They open up a whole world of hiking I would never have imagined enjoying.  Nothing beats a sunrise hike — witnessing a sunrise from a mountain summit is an absolutely magical experience.

Similar Hikes

Any hike that includes Twin Mountain is a great hike. Twin can be climbed from Indian Head, from Jimmy Dolan Notch, or from the Sugarloaf / Dibbles Quarry side.

This is one of the most scenic Catskills hikes.

Because of the rock scrambles and technical nature of the Devil’s Path, this is a difficult hike.

If you’re looking for a more challenging hike, try Rocky & Lone via the Fisherman’s Path or try hiking Friday, Balsam Cap & B25 Crash Site from Moonhaw.

The parent mountain for this hike is Indian Head.

If you do this hike, LMK how it went…

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