Escarpment Trail

Tracing a path over some of the Catskills’ most famous mountains, the Escarpment Trail in New York state is a challenging and picturesque backpacking trip well suited for hikers looking for a highlight reel of the region. I hiked the trail southbound in June 2026 with my friends Eric and Pete as a two-night excursion to escape the summer heat and enjoy some famous vistas.

At 24 miles, the Escarpment Trail isn’t particularly long, but there are a few complicating factors.

The first choice to make is which direction. A number of the guides showcase a Northbound trek starting near Kaaterskill Falls and ending after Windham High Peak. We chose the opposite, starting near Elm Ridge Wild Forest and ending at North-South Lake. Southbound saves the best and most famous views for last, and allows for hikers to ascend, rather than descend, the steepest parts of Blackhead Mountain. We also liked the idea of a challenging second day followed by a rewarding and scenic third.

It’s an end-to-end hike, so you’ll either need two vehicles or to use a shuttle. With three of us hiking, a two-car solution was simple and we chose to do that, with one of us parking at the Scutt Road Parking Area and carpooling to our start on Route 23 in East Windham. Parking is free and requires no permit, but in busy seasons the lots may fill and be closed. For a shuttle, I’ve read good reviews about Rip Van Winkle Adventure Guides.

Permits aren’t required and wild camping is fine 150 feet from the trail, but camping is not permitted above 3500′ in the area. Luckily, areas above this elevation are clearly marked with signage indicating this, and we didn’t see many appealing campsites that high up anyway.

Water is scarce on the ridge, so you’ll need to pack accordingly and expect extra mileage if you stock up mid-trail. We were pleasantly surprised by the quality of water we found – the stream near the Batavia Kill shelter is delicious – but weren’t as thrilled with the extra climb. In the autumn, I’d expect some of these water sources to be even drier.

Finally, bears aren’t terribly common in the area and in fact we saw few mammals in general on the trip, but we packed a bear can regardless.

Our first day on the trail was short – basically a head start – and began at the parking area for the Elm Ridge Wild Forest on Route 23 in East Windham. With only a mile and a half to hike, we set out around 6:30 in the evening and began hiking through the meadows and deciduous forests below the shoulder of Windham High Peak.

Before long we were at our destination for the evening, the Elm Ridge Lean-to. The shelter was occupied by a mother & daughter hiking Windham, so we set up camp in the grassy area behind it. Complete with ample hiking space and a well-appointed privy, this was a perfect stop for night one. The three of us enjoyed a sub sandwich dinner and tucked in for an early night before a big day two.

Day two started with clear skies and beautiful, temperate weather. Our itinerary was aggressive: 14 miles of rocky hiking with three large ascents: Windham High Peak, Blackhead Mountain, and Stoppel Point, totaling 4000 feet of gain if we didn’t have to descend for water and more if we did.

Windham High Peak is frankly a great start to the day, with its gradual ascent and relatively rock-free trails. We began climbing around 8:30 in the morning and were quickly rewarded with sweeping views.

Between the climbs, the defining feature of the Escarpment trail has to be foliage & plant life. Lush, verdant ridge walks are interspersed with views of the blanket-like forest. Flowers, grasses, and deciduous & spruce trees are arrayed out vertically, changing as we constantly ascended and descended through different ecological zones.

We covered mileage really well across Windham High Peak and the ridge to its east, hiking past Burnt Knob and over Acra Point.

After a few hours on the trail, we were ready for lunch and to refill water. The Batavia Kill Shelter was 8 miles into our walk and an ideal spot for a bite and a drink. Just before Blackhead Mountain, we headed down the Batavia Kill Trail to the shelter and campsite area, costing us a half mile and a few hundred feet of descent, but earning us a resupply of water and a great place for a snack.

Batavia Kill – the creek that trickles down the west slope of the ridge – was a clean source of water for us. In the autumn I’d expect it to be drier, but in June we had clear, moving water to filter and enjoy. We topped up on hydration and enjoyed a charcuterie lunch in the shelter, which is situated in a wide grove filled with tent sites. If we had had more time on day one, this would have been a great camp for the night, but we were happy to use it as a midday waystop regardless.

After the break we donned our gear and began climbing Blackhead Mountain, the steepest climb of the trip and the highest point on the trail.

This region is famous for its legacy in American painting, specifically the Hudson River School. Founded by Thomas Cole, the movement spawned a generation of artists who captured the region’s stunning vistas, ledges, and forests in remarkable detail. Climbing Blackhead however, felt much different. It’s darker, deeper, and rootier; not nearly as bright and airy as the paintings of the region usually depict. Ascending under the hazy & dark canopy, I was reminded less of Cole’s work than I was of Friedrich’s Man and Woman Contemplating the Moon.

After a steep and scrambling climb, we made it to the top of Blackhead. The summit is wooded, but a few breaks in the trees provide sights to enjoy. On the southern side of the mountain, the descent is steep but not as aggressive as the climb – another good reason to hike this trail from Windham to Kaaterskill.

We descended into Dutcher Notch and appraised our water situation; there is a spring a half mile down the crossroads that one of the last places to camel up before a long stretch of dry ridges. We had enough for the remainder of the day, so we began climbing up towards Stoppel Point.

Halfway up the three climbs that ascend to Stoppel, one of the Catskills’ famed squalls blew in from the west. Dark clouds, strong winds, and dropping temps were accompanied by a cascade of rain. As quickly as the showers came, they passed us by and left us with a tremendous rainbow to enjoy.

Atop Stoppel Point, we encountered the crash site of N1316T, a Piper PA-28 that suffered a fatal crash into the mountain in 1983. The site is a reminder of the many aviation accidents that have occurred in the region, no doubt in part due to the dynamic terrain and unpredictable weather that we had just experienced.

After Stoppel Point, we descended onto the wide plateau just west of North Mountain and began looking for campsites for the night. Eventually, we settled in to a comfortable grove of pines, where we had a hasty dinner and got to bed early, eager to escape the rapidly falling temps.

A brisk wind and a cold front dropped temperatures on night two to only a few degrees above freezing, making it a challenge to rustle ourselves awake early in the morning. Luckily, the final day was all downhill and also treated us to some of the best views of the Escarpment Trail.

At North Point, it became clear why Thomas Cole and his compatriots took so much inspiration from The Catskills. The view to the south provides a stunning survey of North-South Lake, the surrounding mountains, and the Hudson River Valley to the east. For much of the day, we would essentially be hiking through the landscape portrayed in one of Cole’s most famous works.

Descending off North Point, the views get better and better. Newman’s Ledge provides an exceptional panoramic view of the Hudson River, and is a perfect nesting place for peregrine falcons during their breeding season. During some times of the year, the trail here may be closed or re-routed in order to protect the habitat for the birds.

The trail here became remarkably busy with day hikers, dog walkers, and children running about. We also met a number of folks running Manitou’s Revenge, a 53 mile ultramarathon that uses the Escarpment Trail for its initial leg.

At North-South Lake and the old Catskills Mountain House area, ample parking meant tons of families were spending the holiday weekend picnicking and enjoying the weather.

After a short climb up South Mountain, the Escarpment Trail runs on old carriage roads for a few miles before beginning its final ridge walk overlooking Poet’s Ledge, Kaaterskill High Peak, and Round Top.

The scenes along the last stretch of trail are phenomenal and constitute some of the nicest views on the East Coast. Once we reached the Frank D. Layman Memorial, we turned away from the ridge and began the final segment back to Scutt Road.

In less dry weather, we would have likely made a stop at Kaaterskill Falls, but given the crowds – several hundred people were making their way to and fro – and the lack of river, we skipped it and focused on wrapping our trip up.

Finally we made it the terminus at Scutt Road. The lot was completely full with dayhikers and tourists, a far cry from the quiet parking area we had left two nights before. We congratulated each other, hydrated, and hopped in to shuttle back to the remaining vehicle in Windham.

The Escarpment Trail is a wonderful weekend trip that showcases some of upstate NY’s most famous sights. Although water can be tricky, the trail is broadly logistically easy and contains a perfect mix of challenge and awe.

Go hike it!