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Routes
Hiking trails & Routes
United States
New York
Greene County

Devil's Path: Indian Head, Twin, and Sugarloaf Loop

Routes
Hiking trails & Routes
United States
New York
Greene County

Devil's Path: Indian Head, Twin, and Sugarloaf Loop

Hard

3.0

(29)

40

hikers

Devil's Path: Indian Head, Twin, and Sugarloaf Loop

09:51

23.6km

1,340m

Hiking

Hike the Devil's Path: Indian Head, Twin, and Sugarloaf Loop, a difficult 14.7-mile route with 4381 feet of gain and stunning Catskill views

Last updated: February 26, 2026

Tips

Includes segments that may be dangerous

Parts of this route comprise highly technical, difficult, or hazardous terrain. Specialist equipment and prior experience is required.

After 4.28 km for 1.14 km

After 5.53 km for 7.93 km

After 18.3 km for 2.37 km

Waypoints

A

Start point

Parking

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1

5.42 km

Sugarloaf Mountain Overlook

Highlight • Viewpoint

The top of Sugarloaf Mountain offers an open view of the Ashokan Reservoir and surrounding hills.

Tip by

2

7.98 km

Twin Mountain Overlook

Highlight • Viewpoint

At 3,650 feet, Twin Mountain is one of the most popular hikes in the Catskills. You will reach the summit via a ridge traverse along Devil's Path with the option …

Tip by

3

10.3 km

Indian Head Mountain Viewpoint

Highlight • Viewpoint

Indian Head Mountain gets its name from its long summit profile. The views are really pretty from here!

Tip by

B

23.6 km

End point

Parking

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Way Types & Surfaces

Way Types

12.0 km

11.5 km

< 100 m

Surfaces

11.5 km

8.01 km

4.00 km

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

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Today

Monday 18 May

28°C

17°C

23 %

Additional weather tips

Max wind speed: 14.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How challenging is the Devil's Path: Indian Head, Twin, and Sugarloaf Loop?

This loop is consistently rated as "difficult" and is considered one of the most challenging and potentially dangerous hiking paths in the East. It features rugged terrain, steep ascents and descents, and requires occasional hand and foot use for climbing. Expect a demanding experience with significant elevation gain and varied terrain.

What is the terrain like on this trail?

The trail features a demanding and varied terrain, characterized by steep ascents and descents, numerous rock and root scrambles, and tricky rock chutes. Hikers should be prepared for vertical climbs, including a particularly difficult 30-50 foot section up a nearly sheer cliff where small tree roots may be needed for assistance. Muddy sections can also be present.

What are the main viewpoints and highlights along the route?

Despite its demanding nature, the loop offers spectacular views. You'll find notable vistas at the Sugarloaf Mountain Overlook and the Twin Mountain Overlook. Near Indian Head, look for ledges offering wide views over the Hudson River. The Indian Head Mountain Viewpoint also provides expansive scenery.

How long does it typically take to complete this loop?

This challenging loop typically takes 8 hours or more to complete, depending on your pace and how often you stop to enjoy the views. It involves substantial elevation gain over its 23.6 km (14.7 miles) distance.

Where can I park for the Devil's Path: Indian Head, Twin, and Sugarloaf Loop?

Common trailheads for sections of the Devil's Path, which this loop is part of, include Prediger Road and Mink Hollow. Parking availability can be limited, especially on weekends, so it's advisable to arrive early. There are no shuttles specifically for this loop.

Are permits or entrance fees required to hike in the Catskill Park?

No, there are generally no permits or entrance fees required for day hiking on public trails within the Catskill Park, including the Devil's Path. However, always check for any updated regulations or specific requirements for camping if you plan an overnight trip.

Is the Devil's Path: Indian Head, Twin, and Sugarloaf Loop dog-friendly?

Dogs are generally allowed on trails in the Catskill Park, but they must be kept on a leash at all times. Given the extreme difficulty and rugged terrain of this specific loop, including vertical scrambles, it may not be suitable for all dogs, especially smaller or less agile ones. Consider your dog's capabilities carefully.

What is the best time of year to hike this trail?

The best time to hike this trail is typically during the late spring, summer, and early fall. Fall offers spectacular foliage, but can also bring colder temperatures and wet leaves making the already challenging terrain more slippery. Winter hiking is possible but requires specialized gear and experience due to ice and snow.

Does this loop intersect with other well-known trails?

Yes, this route utilizes significant portions of the famous Devil's Path, covering about 58% of the loop. It also incorporates sections of the Long Path (48%), Mink Hollow Trail (22%), Pecoy Notch Trail (18%), and Jimmy Dolan Notch Trail (16%).

What should I pack for a hike on the Devil's Path: Indian Head, Twin, and Sugarloaf Loop?

Given the trail's difficulty and length, you should pack essentials like plenty of water, high-energy snacks, a map and compass or GPS device, a first-aid kit, and appropriate layers of clothing. Hiking poles are highly recommended to aid with the challenging ascents and descents. Sturdy hiking boots with good ankle support are a must.

Are there any less challenging alternatives nearby for beginners?

While this specific loop is very difficult, the Catskill Park offers many other trails. For less strenuous options, you might look for trails around North-South Lake Campground or other state land areas that offer shorter distances and less elevation gain. Always check trail descriptions and difficulty ratings before heading out.

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