Westchester Wilderness Walk (Pound Ridge, New York)


This loop hike follows winding paths past interesting natural features through a 150-acre preserve in Pound Ridge, in the heart of Westchester County.

4 hours
Easy to Moderate
6 miles
Route Type:
Allowed on leash
Views, Woods, Birding, Wildflowers
First Published:

Daniel Chazin


Westchester Wilderness Walk


View Westhcester Wilderness in a larger map

Trailhead GPS Coordinates
Driving Directions

From I-684 take Exit 4 (Mount Kisco/Bedford). Turn east at the bottom of the ramp and follow NY 172 through Bedford Village. At a Mobil gas station, turn right onto Long Ridge Road. In 2.5 miles, turn left onto Upper Shad Road and continue for 0.3 mile to a small parking turnout on the left side of the road. The trailhead is marked by a small green sign for the Zofnass Family Preserve.


The Westchester Wilderness Walk might not fit the dictionary definition of “wilderness.” The area is criss-crossed with stone walls, remnants of the early settlements in the area, and houses may occasionally be seen from the trails. But remarkably, for nearly the entire hike, one is entirely removed from the surrounding civilization of Westchester County. The trails have been routed – often, quite circuitously – to pass many unusual and interesting natural features, resulting in a hike that will probably seem longer than the map appears to indicate. The walk is a unique experience that is well worth the 40-mile drive from the George Washington Bridge!

The trails in the preserve form five loops, four of which will be covered in this hike. They are blazed with green plastic markers and blue paint blazes on rocks. Many of the trails are bordered by logs. However, the hiker should be alert for sharp turns, some of which are easily missed, especially if the ground is covered with snow.

The trail begins at a kiosk just beyond the parking area, where a map of the preserve is posted. Take time to read the inspiring story of the assembly (without any public funding) – over a period of 20 years – of various private lots into the preserve by Paul Zofnass, a Manhattan investment banker. The trail continues along a Woods road near the entrance. Photo by Jane Daniels.woods road, with a wetland on the left. It soon passes, on the right, the start of the West Loop. This will be your return route, but for now, continue straight ahead. A short distance beyond, a sign on the right marks the Princess Pine Grove – named for the tiny club moss found in the area. This is the first of many named natural features along the trail, most of which are marked by signs.

Soon, the trail narrows to a footpath and crosses several streams on rocks. When you reach a T-intersection, with a wooden bridge on the right, turn left and cross a rock causeway, with a wooden handrail, over a stream. Just beyond, you’ll come to a junction, where the South Loop begins. Turn right and follow the loop in a counter-clockwise direction. Upon reaching Becky’s Brook, the trail turns sharply right and soon passes the ruins of Tom’s Cabin. A short distance beyond, you’ll climb rock steps in a narrow passage between two rocks and reach Trudeau’s Point of View.

When you arrive at the South Loop Short Cut, turn right to continue on the main loop. After descending a little, you’ll pass various plaques that recognize the dedicated efforts of the Zofnass family in protecting the preserve. You’ll go by a wetland bordered by well-laid stone walls, then cross a paved private road and passStone Puncheon. Photo by Jane Daniels. several more plaques. Just beyond, bear right at a junction, following a sign for the Main Trail.

After crossing a wet area on rocks, the trail climbs a rock stairway to reach Tulip Tree Heights. A short distance beyond, you’ll arrive at Jessica’s Junction, where you should turn right to follow the Roundabout in a counter-clockwise direction. Then, in about a quarter of a mile – after passing a stone bench at Mossy Knoll – you’ll reach another intersection. Here, you should turn right onto the “lollipop stick” of the East Loop.

After a relatively level section, you’ll reach the top of the Grand Stone Staircase. Two routes are provided to descend this interesting feature, with the left route designated as “easier” and the right route “harder.” Neither route is particularly difficult, but you will be returning this way, so you may wish to select the “easier” route for the descent and the “harder” route for the ascent on the return.

After a short descent, you’ll reach an intersection where the East Loop proper begins. Bear right to follow the loop in a counter-clockwise direction. You’ll cross a wet area on large rocks, climb a little, then turn left onto a woods road, with a large wetland to the left. When you reach a sign “Out to Upper Shad .1 m,” turn left to continue along the trail.

At the end of the wetland, you’ll come to another paved private road. Turn left and follow the road for 250 feet, crossing the outlet of the wetland on the road bridge, then turn left, cross a small stream on a rock bridge, and reenter the woods. This is about the halfway point of the hike. The trail now follows a rather rugged footpath along the northeast shore of the wetland, with several cliffs looming above to the right.

When you reach the end of the loop at the northwest corner of the wetland, turn right, following the sign for the Central Roundabout. You’re now retracing your steps along the “lollipop stick” of the loop, going back up the Grand Stone Staircase and continuing to the junction with the Roundabout. Here you should turn right, following the sign “Roundabout (continued).”

The trail descends to cross a stream on large rocks. A short distance beyond, it climbs to Over the Top (a rock outcrop to the left of the trail) and descends to Moss Falls, a huge boulder covered with moss. It then climbs to Razor Ridge Rock. After paralleling a stone wall, the trail turns left, making a sharp U-turn, and descends. Be alert for this turn, which is easily missed.

The trail circles the interesting Roundabout Rock and soon arrives at another junction. Here, you should turn left, following the sign “Roundabout to South Loop.” Immediately, you’ll cross a stream on rocks. After briefly paralleling the stream, the trail bears left and begins to head south.

At the next junction, you should turn right at a sign “South Loop – to Kiosk” and go through Wedge Walk Rock, a narrow passage between two boulders. You’ll soon pass the aptly named TV Antenna Rock and descend to a stream. The trail turns right and follows along the stream on large rocks, with the stream directly below (this section of the trail is marked with blue paint blazes). After a short distance, the trail turns left and climbs rock steps to the left of a large boulder. It passes Fowler’s Rock and Pauley’s Point Rock and then runs near the edge of an escarpment, with views over a wetland below.

After curving to the left and descending, the trail passes Jurassic Rock and soon begins to run along the wetland. It loops around to cross one end of the wetland on rocks and passes the Triple Red Oak. Then, at the next junction, turn right, following the sign for “Quest” (don’t follow the South Loop Shortcut).

The trail makes a long loop to the southwest, passing Layer Cake Rock, Lichen Ledge, Tulip Tree SqueezeLichen Ledge. Photo by Jane Daniels. and Cantilever Rock. After paralleling a long, slanted rock, it makes a sharp U-turn and begins to descend on switchbacks. Near the base of the descent, it follows stone steps along an attractive cascade. It continues on a level path alongside a wetland.

In a short distance, you’ll notice a sign for the West Loop Trail on the right. Turn right and follow this trail, which parallels several rather tall and thick stone walls, then climbs a little and winds through stands of cedar. After passing Mayo Fort, the trail descends on switchbacks to a T-intersection by a stone wall, where you should turn right.

The trail now heads along the Western Wetland Walk, with a wetland on the left and a stone wall on the right. For much of the way, you follow stepping stones over wet areas. At the end of the wetland, the trail turns left, crosses the outlet of the wetland on a rock bridge, and soon reaches a T-intersection just north of the main entrance. Turn right to return to the kiosk where the hike began.

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I live in Mt.Kisco and have

I live in Mt.Kisco and have been to Westmoreland, Butler and Mianus River Gorge many times, yet never knew this existed until yesterday. There's something almost magical about this preserve, it has a very Fairy Tale Forest feel. I thought maybe I'd come across a cabin made of candy or a house with 7 dwarves living in it. Either that or it was all laid out by Olmsted. It'seasy to lose your bearings the way all the trails turn on a dime. I love the story about how Paul Zofnass created the preserve. It's nice to see people doing goodthings with their money. The NY Times had an article explaining how it was done.  

Nice little park

Nice little preserve with enough trails to do a reasonably long hike. We found this hike very peaceful - very little car noise (only near the trailhead) for such a suburban area. Small parking area - fits around 3, maybe 4 cars.   We found an online map here: http://westchesterlandtrust.org/?page_id=1418 All of the trails use the same green blazes, even though the map shows colored loops. The trail intersections are well marked though (e.g. "Central Roundabout Clockwise", and some intersections even have "you are here" maps.   Some photos: http://agiletrekker.blogspot.com/2015/05/westchester-wilderness-walk-zofnass.html