Devil’s Path — Indian Head to Twin Mountain

What to bring

Day-hike essentials for this trail. As an Amazon Associate we earn from qualifying purchases.

LOWA Renegade EVO GTX MidGORE-TEX, 3 widths, resolableCheck price on Amazon →Hydro Flask Wide Mouth 32ozinsulated, durableCheck price on Amazon →Osprey Talon 22ventilated back, pole carryCheck price on Amazon →Adventure Medical Kits Ultralight Watertight .7day-hike specific, waterproofCheck price on Amazon →Black Diamond Spot 400-Rrechargeable, comfortableCheck price on Amazon →

What to Expect

The Devil’s Path is widely considered the hardest day hike in the Northeast, and the section from Indian Head to Twin Mountain earns that reputation honestly. The full 24-mile route crosses six peaks with 9,000 feet of cumulative gain, but most people tackle it in sections. The Indian Head to Twin Mountain segment is 6.2 miles out and back from the Prediger Road trailhead, gaining 2,400 feet with two summit crossings — Indian Head at 3,573 feet and Twin Mountain at 3,640 feet.

The trail doesn’t ease you in. It climbs hard from the start, with steep rock slabs and scrambles on every ascent and descent. Indian Head has a south-facing viewpoint with a sheer drop looking out toward Woodstock and the Hudson Valley. The ridge walk between Indian Head and Twin follows a narrow col through dense spruce and fir. Twin Mountain’s summit is wooded but there are partial views through the trees on the west side. The real payoff is the climbing itself — this trail is physical and relentless in the best way.

If you want more, the Devil’s Path continues west to Jimmy Hollow and Sugarloaf Mountain, but the Prediger Road out-and-back is a full day for most fit hikers. Know that every foot you gain going out, you lose coming back. The return trip over Indian Head from the west is the crux — steep, loose, and unforgiving when your legs are already spent.

Difficulty

Strenuous. This is not a casual trail. The 2,400-foot gain in 6.2 miles sounds manageable on paper, but the scrambles on Indian Head demand hands and feet, and the descent off the back side of each peak is technical. Loose shale, exposed roots, and short vertical drops are standard. Trekking poles help on the descents. Budget extra time coming down compared to going up. This is a trail for experienced hikers who are comfortable on exposed rock. If you haven’t hiked with significant scrambling before, do Giant Ledge or Wittenberg first.

Best Time to Go

Late September through mid-October for foliage, with the caveat that wet rock on the scrambles is genuinely dangerous. Dry fall days are ideal. Spring works once the mud settles, usually mid-May, but snow lingers on the north-facing slopes into April. Summer is fine — the shade from the spruce forest keeps it cooler than the lower peaks. Avoid this trail in wet or icy conditions. The exposed slabs on Indian Head are treacherous when slick. Weekends in October bring crowds to the parking pullout on Prediger Road, which has limited space. Arrive before 8am.

Before You Go

The Prediger Road trailhead is off Route 214 in Hunter, about a 2.5-hour drive from Manhattan. The parking pullout is small — maybe 10 cars. No facilities at the trailhead. Bring at least 3 liters of water; there’s no reliable source on the ridge. Bug spray is useful in June and early July. Cell service drops quickly on the approach. Let someone know your plans and estimated return time. Dogs are technically allowed but the scrambles make this trail rough on most dogs. Wear real hiking shoes with ankle support.

Gear for this hike

Our day-hike checklist — the picks that show up again and again from tested gear roundups. As an Amazon Associate we earn from qualifying purchases.

LOWA Renegade EVO GTX MidGORE-TEX, 3 widths, resolableCheck price on Amazon →Hydro Flask Wide Mouth 32ozinsulated, durableCheck price on Amazon →Osprey Talon 22ventilated back, pole carryCheck price on Amazon →Adventure Medical Kits Ultralight Watertight .7day-hike specific, waterproofCheck price on Amazon →Black Diamond Spot 400-Rrechargeable, comfortableCheck price on Amazon →Patagonia Torrentshell 3L Jacketdurable, trail + everydayCheck price on Amazon →Darn Tough Hiker Micro Crew Midweightlifetime warrantyCheck price on Amazon →Black Diamond Pursuit Trekking Polescork grip, lightweightCheck price on Amazon →Sawyer Squeeze Water Filterultralight, standard threadsCheck price on Amazon →Sawyer Premium Permethrin Insect Repellent Spraytreat clothing; kills ticksCheck price on Amazon →Mountain Hardwear Crater Lake Long Sleeve HoodyUPF 50, hood + thumb holesCheck price on Amazon →