Trip Report · 2025-06-29

Region: Catskill · Confidence: High · Reporter: Intermediate · Created: 2026-06-27 17:29

Summary

Hiker completed a morning ascent of Twin and Indian Head via the Jimmy Dolan Trail on June 29th, starting before dawn from the Prediger Road trailhead. The well-maintained trail with good stonework and lookouts provided pleasant conditions, though the hiker was unable to locate the reported cliff view on Indian Head.

Peaks

Tags

drytrail-improved

Source

Raw body (2910 chars)
Got an alpine start from New Jersey this morning, Sunday, June 29th. Thankfully, I managed to creep out without waking anyone, not even our usually unrelentingly alert guard doodle.
I’ve had a very rough and idle winter and spring, plagued by a calf injury and kept distracted by the general pandemonium of a new baby in October and a new job in January. This was only my second day in the woods all year so far, the first being a hike up Blackhead in January. My physical activity the last six months has consisted almost exclusively of pushups, the occasional run, and the stationary bike at odd hours.
After a quick, two-podcast drive I pulled into the Prediger Road trailhead around 4:45 am. There were several cars in the parking lot, four or five, and one tent. I was pretty much able to start with no headlamp. I needed the light to sign in, and to notice that I was the first name in the book for the day, but didn’t need it on the trail.
I went up the Jimmy Dolan Trail, with two out and backs to Twin and Indian Head on the itinerary. I couldn’t wait to finally see for myself the spectacular cliff on Indian Head overlooking the lake that all these people post about on Instagram. 👍
The Jimmy Dolan Trail is delightful. I was surprised by how many beautifully placed broad flat stones there were, providing steps and almost a cobblestone path feel. Kudos to the trail builders. Got to the notch in short order and headed to Twin Mountain first. There were scattered clouds and the sun started to creep up as I made it to some views back towards Indian Head and then the very cool lookout on top of the south peak of Twin, which was the best vantage point of the day, in my opinion.
I saw my first other person of the day on the lookout just past the summit of Twin proper: an older guy doing the Devil’s Path solo. That’s definitely on my bucket list, but I’m definitely no where near the shape right now. I guess he was making pretty good time. Not sure exactly what time he started, though after I did at 5:00 ish. He was going east to west, obviously, and was there on the summit of Twin on or around 7:00 am.
After a quick text to check in at home, I doubled back and made my way back towards the notch. Saw a group of four on my descent to the junction, including a dude in crocs. Didn’t even have the little support strap flipped to the back. Ballsy.
Indian Head was good. The climb was easier I thought than that up Twin, but sadly I couldn’t find that cliff overlooking the lake anywhere. Looked all around for it. 😕
Had a chill and uneventful walk back to the trailhead. Jogged a bit on the Jimmy Dolan Trail after the pitch flattened out a bit lower down, which felt good. A good first hike for the season, but I really felt it and have a lot of work to do to get back into shape.
Home by 12:00, which is great. This is Catskill 3500 3/37 for me. (I’m joking about Indian Head, obviously).