Windham High Peak Bushwhack from Big Hollow Road: A Catskill 3500 Loop with First-Growth Mapping
The Route Less Traveled to the Summit of Windham High Peak
There’s something special about a route that starts with a little uncertainty and ends with a summit view. On this hike, we bushwhacked Windham High Peak from Big Hollow Road, crossing NYCDEP land, following old logging roads, and eventually linking up with the Escarpment Trail just below the summit. Along the way, Moe was on the lookout for first-growth forest, mapping locations and using the kind of field awareness that ties directly into the work of Dr. Michael Kudish, whose research has helped define so much of what we know about the Catskills’ forest history.
Windham High Peak Bushwhacks Quick Facts
🧭 Trailhead: Big Hollow Road, Maplecrest, NY (just a pull off - Google Maps)
🗺️ Route: Bushwhack → Escarpment Trail → Bushwhack
🥾 Distance: ~5 miles round trip
📈 Elevation Gain: ~1,565 ft
⚠️ Difficulty: Difficult
Because this is a bushwhack, we don’t share GPX tracks or AllTrails links. Part of what makes bushwhacking meaningful is learning how to read the land, build your own route, and navigate responsibly without creating new social trails or unnecessary impacts on the woods. If you want to build those skills, we offer guided hikes through Hike On Guides as well as training in map, compass, and GPS navigation.
Windham High Peak Bushwhack Overview
This hike begins on a New York City watershed parcel off Big Hollow Road and quickly settles into a mix of old road walking and off-trail navigation. The lower portion of the route follows old roads that suggest the area was once logged before the land changed hands and became part of the larger protected landscape we hike today. As we climbed higher, the route gradually became more of a true bushwhack, with the woods changing character as we worked toward the ridge and summit. We then hit the Escarpment Trail which we followed to the summit of Windham High peak with it’s stunning views. From there we followed the Escarpment Trail down off the summit before leaving the trail and bushwhacking back down to our car.
The transition from old road to forested ridge is one of the best parts of this hike. It gives you that classic Catskills feeling of moving through layers of land use and forest history, where a single route can take you from a logged parcel to what may be much older woodland just a little higher on the mountain.
First-Growth Forest Search
One of the most interesting parts of the day was Moe’s ongoing search for first-growth forest. The Catskills have a long logging history, so finding stands that were never cut is a big deal, and identifying them takes a careful eye for tree size, canopy structure, and signs of disturbance. That’s where the influence of Dr. Michael Kudish matters so much: his work has given hikers and forest historians a framework for recognizing these rare places in the woods. Moe has been working with Dr. Kudish for several years to help map these forests and part of the goal of this trip was to do just that.
Catskills Forest History: Dr. Michael Kudish's The Catskill Forest: A History
Moe’s first-growth mapping on this hike ties directly into the work of Dr. Michael Kudish, whose landmark book The Catskill Forest: A History is the definitive guide to the region’s woodland past. Published in 2000 after more than 40 years of research, Kudish’s book uses maps, tree-ring data, and historical records to trace plant migrations, logging impacts, and forest recovery across the Catskills, including how glaciers, settlers, and industries shaped the woods we hike today.
As we moved higher on Windham High Peak, the forest began to show signs that helped narrow down where first-growth started. We saw places with larger trees, broken tops, exposed ridge conditions, and other clues that made us stop and look more closely. This wasn’t just a climb to a summit, it was also a field day in the woods, with Moe mapping first growth pockets for future reference.
Windham High Peak Summit Views
Eventually, we reached the Escarpment Trail and used it to finish the climb to Windham High Peak’s summit. Windham High Peak is one of the most rewarding Catskill 3500 peaks because it combines a manageable ascent (via the Escarpment Trail from Route 23) with big views and a ridge walk that feels classic without being overly punishing. The summit area gives you wide-open looks toward the Hudson Valley and neighboring Catskill peaks, including the Blackhead range, so the payoff is absolutely there once you top out.
The Return Loop
After spending time on the summit, we hiked down the Escarpment Trail a bit and then left the trail and bushwhacked back down toward Big Hollow Road to complete the loop. The descent had its own challenges, including steeper sections, rockier footing, and the need to stay alert while navigating back through the woods. That’s part of what makes a loop like this satisfying: it’s not just a walk to a viewpoint, it’s a route that asks you to read the land on the way up and again on the way down.
Eventually, we came back onto an old road and followed it out to the car, closing the loop after about five miles. By the end of the day, we had followed old roads, bushwhacked untracked first growth forests, reached a Catskill 3500 summit, found more clues to first-growth forest, and made another good memory in the Catskills.
Why We Loved This Hike
What makes this hike special is the combination of adventure and discovery. We had the satisfaction of a bushwhack, the views from the summit, and the added layer of forest history research that makes the whole outing feel more meaningful.
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For More Information on hiking the Windham High Peak
Catskills Visitor Center
Additional Catskill Park information is available at the Catskills Visitor Center located at 5096 Route 28 in Mt. Tremper.
Hire Hike On Guides for the Windham High Peak Bushwhack
Need help on a hike like this? Both Moe and Jeff are NYSDEC licensed hiking and backpacking guides. Hire us through our guiding company, Hike On Guides for customized trips in New York, New Hampshire, Vermont, and Massachusetts.
Hikes near Windham High Peak
More of our Catskills hikes on YouTube
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Important Hiking Considerations:
Weather: Check the weather forecast before your hike and be prepared for changes in conditions.
Safety: Some sections of trail can be steep and rocky, others can be muddy, so use caution and always watch your footing.
Leave No Trace: As with any outdoor activity, remember to follow the principles of Leave No Trace. Pack out any trash, stay on the trail, and be respectful of the natural environment.
