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A bushwhack route that requires top-notch backcountry navigation skills.
Hiking Trail Description
Bushwhacking from Round Top to Kaaterskill High Peak is a truly delightful hike, peppered with as much history as moss.
This route has become my favorite way to get to the summit of Kaaterskill High Peak. It’s the shortest route, with the lowest amount of elevation gain and, by far, is just the loveliest time from beginning to end.
It also has the least mud—which, if you know Kaaterskill High Peak’s at all, you understand what a big win this is.
This entire route is untrailed. Getting off of Round Top’s summit is tricky. Make sure you are fully comfortable hiking off-trail in the wilderness, and you know how to use a compass.
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Round Top to Kaaterskill High Peak
The Round Top to Kaaterskill High Peak route includes…
- Off-trail hiking the whole way
- Steep terrain
- A stream crossing
- A lot of moss
- Historical spots like the Tory Fort
- Some of The Catskills’ finest views
- A plane wreck (optional)
A full breakdown is provided in the hike notes below, with 21 photos.
Round Top to Kaaterskill High Peak Hike Time
Allow 3-4 hours for this hike.
Round Top to Kaaterskill High Peak Elevation Gain
The elevation gain for this hike is 2,200 feet (apx 670 meters).
Round Top to Kaaterskill High Peak Hike Notes & Gallery
Start at the last parking area on Gillespie Road. See the exact trailhead location at the bottom of this page.

Look for a herd path through the tall grass…

…and, for a short distance only, follow an old road. Then follow a turn-off to the right and head along a flat section until you reach the stream.
You’ve got the basic details, but there’s so much more…
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Similar Hikes
Kaaterskill High Peak has so many adventures in store for you. There are so many great spots all over the mountain.
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Round Top to Kaaterskill High Peak Trailhead
Small rough lot
Google Maps Location: 42.171337, -74.113721
The map below shows the exact topographic location of the trailhead
Cell Service
Okay-ish throughout. Patchy but workable. Mostly. My network is Verizon. YMMV.
The parent mountain for this hike is Round Top.