Windham High Peak via Escarpment Trailhead (Catskill Park)
Hike Type: Out-and-Back
Distance: 7.39 miles
Elevation: 1,788 feet
My Time: 2 hours, 54 minutes
Book Time: 4 hours, 35 minutes
Parking: Ample parking at the Escarpment Trailhead off of NY-23.
Hiking Challenges: Catskill 3500 Club; 52 Hike Challenge 2026; Operation Alaska Benchmark Challenge
Hiking Challenges: Catskill 3500 Club; 52 Hike Challenge 2026; Operation Alaska Benchmark Challenge
The Hike
Time to drive to New Jersey to fly to Florida... I was up at 5:00am and out at 5:50am after packing. I got some breakfast at Stewarts on my way to the Catskills for one final hike. It was a beautiful morning in the low 60s with abundant sunshine. I was feeling a little sore from yesterday's jaunt up Mt. Jefferson, but other than that (and the heavy emotions on my brain), I was off to a good start!
The part of the drive through the Catskills on NY-23 was exceptionally pretty, especially the height of land. I passed a "Five State Lookout," which perplexed me - New York, Vermont, Massachusetts for sure. Maybe Connecticut too? I guess MAYBE New Hampshire on a clear day? Either way, it was beautiful! I made it to the trailhead at 9:12am and there was ample parking. There was a big group of mountain bikers getting ready for a ride, so I took my time getting ready, used the porta potty, and eventually got moving!
[9:24am - Start of Hike]
My hike started past a bunch of meadowy flowers at the trailhead and then a careful crossing of NY-23 with a nice view to Windham High Peak.
[9:26am - Escarpment Trail]
The Escarpment Trail began on the other side of the road and I immediately crossed a bridge over a swampy stream, passed many flowers, and two boardwalks over wet spots - all of it was wonderfully flat! I signed in at the registration box and then hiked over another boardwalk. I was assuming the infrastructure was so good because this area seems manicured for mountain biking in addition to hiking. I passed the "Gold Mine" trail and started to gently gain elevation. The bugs were awake, but only bothersome if I stood still.
I crossed a stone wall and then crossed it again on this gently winding trail. It was nice and wide, so I was not catching spider webs (thank goodness). Per usual, I found myself photographing all of the blue trail discs in my never-ending quest to find all the different varieties (there WILL be a day where I get a spreadsheet together and turn it into a challenge). I passed the upper junction of the Gold Mine Trail and Trail Six just a few minutes later. I found the Escarpment Trail to be just delightful! It would be an absolute dream if it stayed this way.
Deeper in the woods, the air became warmer and a bit more humid before zigging to the right and zagging to the left, leaving the old road grade. The trail zig-zagged again on gentle switchbacks, which was just wonderful on my tired legs. I spooked a young deer and caught up to two bikers who took off once I caught up - this last straightaway felt like an old road again. The trail made a wide, sweeping left turn, and then came to the junction with the Elm Ridge Trail!
[9:56am - Escarpment Trail/Elm Ridge Trail]
[9:58am - Escarpment Trail/Elm Ridge Lean-To]
There was a big junction sign - I turned left to stay on the Escarpment Trail. Just after on the right was a spur path to the Elm Ridge Lean-To (unsigned). I passed some of those unique yellow flowers that hid the stinging nettles last week on the spur path, and the lean-to area was big and open with tentsites and a privy. It was nice!
Back on the Escarpment Trail, I was now actually hiking, and my quads were NOT happy about it! I will say, this hike would have been a breeze for me if I didn't hike yesterday. I passed some absolutely delightful clover patches and another deer that was incredibly uninterested in moving off of the trail until I was in a full-blown conversation with it and ~10 feet away. When it ran away, three more deer followed, including one majestic looking buck.
I found a trail marker from '69 (nice) and continued to moderately gain elevation before leveling out in a grassy area and crossing a stone wall. This flat area was really pretty - tall pines with very few needles and a low understory - maybe it's so open because of a disease of sorts? I passed another old trail maker, enjoyed a nice breeze, and passed a state land/no camping sign just after hitting the two mile park.
I continued my hike through more beautifully flat and open pine forests, passed another '69 marker, and hiked over some boards lined with flowers. Two trail runners passed me while having a completely normal conversation and somehow not out of breath? Insane. There was a very short steeper push before another flat, and then the Escarpment Trail began to easily ascend again.
The trail brought me over a dry streambed as the trail became more eroded and a few more moderate stretches began to appear. I crossed paths with a guy while the trail was now fully kicking my butt, but again, that's fully due to how tired my body was - the trail was literally fine. I noticed a seemingly random white diamond plastic blaze up on a tree, and then I caught a tree view on the right to a mountain across the valley - either Thomas Cole or Camel's Hump. I caught a peek-a-view to Blackhead on a steeper stretch, too. It was hazy out and that steeper push took the wind out of me! Thankfully the trail went back to easy-moderate after that.
The climb became easier as I approached the sky and the undergrowth was DENSE. There were some muddy spots now that we were higher up and flat again, but overall the trail was in great shape. There were nettles as far as the eye could see with some not-yet-ripened wine/raspberry bushes. It seemed like there would be some beautiful tree views in the winter time from this higher plateau.
[10:55am - Escarpment Trail/3500' Marker]
I was delighted to pass the 3500' sign - the first one of these I'd seen in a long time! I turned onto the ridge and then there was a view spur on the right to a great viewof Blackhead and Black Dome - I am flirting with hiking those on my return trip from Florida. There was a life-saving breeze from the viewpoint. A few feet further down the trail was another view on the left to the valley and lowlands. The flies on the ridge were awake but not dreadful, and the trail wonderfully rambled along the sunny ridge.
[11:01am - Escarpment Trail/Windham High Peak Summit]
To my delight, the summit was marked with a disc! I happily gave it a boop, and noticed that AllTrails had the hike continuing just a little further down the trail, so I followed it, and saw another disc! The viewpoint further down was by far the best and most expansive of the day. It was pretty hazy out so I couldn't see too much, but I'd imagine that the Berkshires and Southern Greens would be in view on a nicer day. There was some old rock-chisel graffiti at this ledge, too.
[11:05am - Escarpment Trail/Return Trip]
I didn't stick around for long as I needed to get down to New Jersey, so I said my thank-yous to the mountain and started my trip down, especially excited for the breakfast sandwich that I left on my dashboard. I was happy with the small number of people that I ran into, especially considering that it's a summer Saturday. I did cross paths with two people at the dry streambed and two more in the land of super tall pines. I was really loving this trail.
[11:53am - Escarpment Trail/Elm Ridge Trail]
I noticed a '67 trail marker just before the lean-to, and at the junction with the Elm Ridge Trail I passed a hiker with a leashed dog and three bikers hanging out talking about past adventures. Time to blast off!
There were more people out now - I had a spectacular trip right in front of a woman and there were two more hikers just behind her. Afterwards, I crossed paths with a guy walking his dog and his bike simultaneously, and a trio after them. The Escarpment Trail zig-zagged down until it was on the gentle, wide road bed again and passing the mountain bike trails. I crossed paths with a trio that was having a BAD time in jeans, cotton t's, and a single Poland Spring water bottle. I crossed paths with another solo hiker (I forgot normal people start in the afternoon) as NY-23 started getting louder.
I wiggled around the old stone wall from before, hit the boardwalk, signed out, hit two more boardwalks, and then crossed the bridge!
[12:18pm - Escarpment Trail Terminus]
I passed a family of four that did not look ready for a hike, carefully crossed NY-23, and happily made it back to my car in one piece.
[12:21pm - End of Hike]
My car's dashboard kept my Meat Lovers Bagel Sandwich from Stewards nice a hot - it was DELICIOUS and ENORMOUS. Perfect! Apparently, I-87 was super backed up, so I ended up driving on back roads all the way to Dad's house in Lake Hopatcong. The drive through the Catskills was stunning (the wind in the notch between Plateau and Hunter was STRONG), I stopped a couple times for Pokemon Go, and coincidentally drove right past the farm my mom grew up on, which felt a little... poetic? It felt special. Especially considering the purpose of this drive...
Step-by-Step
- Follow the Escarpment Trail from the trailhead to the summit and back.
