Family-Friendly Hikes Near Westchester :: The Catskills Part II

I’m back on the trail for Westchester County Mom! If you’re like me and enjoy a day trip for a family hike or vacation in the Catskills, this is for you.

If you haven’t checked them out, you can find all my tips for hiking with young kids.

If you haven’t read up on my Family Hike Challenge Factor, here’s the rundown: This metric runs on a scale of 1 to 5, with 1 meaning the hike is great for all ages and abilities, 3 indicating a hike that offers a challenge but could be accomplished with younger children who have some degree of safety awareness, and 5 indicating leave younger children at home, because you’re in for a real workout!

Bring your swimsuits for this fun hike! While not stroller-friendly, the trail out to Diamond Notch Falls from Spruceton Road is an easy stroll for even the youngest family members. The round trip distance is about a mile and three-quarters of gently sloping land (uphill there, downhill back) along beautiful West Kill. There is not one but two beautiful falls and a swimming hole deep enough that even adults will enjoy the dip. Pro tip – get to the trailhead extra early; it fills up quickly, and the lot is tiny.

Preview trail highlights here. Navigate the trail on AllTrails.

This hike comes with a disclaimer: To get to the lower falls, you’ll first have to contend with almost 200 steps that descend about 400 feet. The steps are narrow and stone, and there is no railing. The stairs and lower trails can be wet and slippery, and beware of flash flooding if rainstorms are in the forecast (speaking from experience).

The good news? The viewing platform for the upper falls is stroller—and wheelchair-accessible and only a quarter of a mile from the parking lot! You also won’t contend with slippery conditions since you’ll view the falls from above.

Whatever route you choose, you’ll be grateful you went. A visit to Kaaterskill rewards you with stunning views of the tallest falls in NY and one of the tallest in the northeast. The power and beauty of the moving water at this site once inspired artists and writers, and you’ll no doubt understand why when you add this to your list of Catskill stops.

View trail highlights here and here. Navigate on AllTrails here.

Pratt Rock is a fun little hike up a hill containing stone carvings from one of the area’s famous figures. The hill is a little steep but not unmanageable for kids who can be safe around drop-offs and narrow trails. If you want stellar views, head up a bit further for mountain and valley views of the western Catskills.

Situated below Windham High Peak (though up the mountain on the plateau), this hike brings visitors through lower-elevation forests and wetlands. Be cautious; the trail is mixed-use and permits mountain bikers (though everyone we encountered was happy to share the trail with hikers). The loop is short, about a mile and a half, and is relatively flat. This makes it great for younger hikers, who will enjoy the rock formations, nature, and bridges throughout the forest preserve. The trail is not stroller-friendly but is easy for the entire family to complete.

Want the payoff of an escarpment hike without all the work? The old Catskill Mountain House site is the perfect solution! The hike from the North-South Lake State Campground parking lot is about a quarter of a mile, and the hill isn’t particularly steep. The path is wide, though the rocks used as gravel are quite large, making it a bit hard to navigate with anything but an off-road jogging stroller.

However, the site was filled with families with young children and plenty of seniors, including at least one with a cane. I hope you gain from that observation that this hike is perfect for the entire family. Once you reach the site of the old hotel, you’ll find east-facing views of the Hudson Valley, Massachusetts, and Connecticut. You’ll feel like you are on top of the world without breaking a sweat.

Windham High Peak’s summit tops out at just over 3500’, making it one of the tallest mountains in the Catskills. Despite its status as a “high peak,” the hike is one of the easiest in the region regarding summit access. This makes it the perfect introductory mountain for those hoping to bag all 33 high peaks and gain entry into the Catskill 3500 Club. It also makes it a great family hike for older kids.

The accent can get steep, verging on scrambles towards the top, and the trail gets incredibly narrow as it runs alongside steep drop-offs. For those able to make the nearly 3-mile trek uphill, the hike pays off with stellar views south to the Blackhead Range and north/northeast over the Durham, Hudson, and Mohawk Valleys and the Adirondack Mountains.

Because Windham is situated at the northwest corner of the escarpment, the prominence on the northwest side is nearly the entire elevation of the mountain (since the Hudson River lies at sea level). This makes a mountain that is otherwise small by world standards feel far larger. Because the round trip hike from Peck Road is almost 6 miles, and due to mountain conditions, this hike is best for older kids (though exceptions exist; a 4-year-old was recently admitted into the 3500 Club… but don’t let that phenom get you feeling bad about yourself – hiking is about getting out into nature, not competition).

1. Family Hikes Near Westchester County :: The Hudson Highlands
2. Family-Friendly Hikes Near Westchester :: The Catskills
3. Family-Friendly Hikes in Westchester (and Beyond)

And be sure to follow my adventures on Instagram at Mama’s Hiking the Hudson! You’ll find hiking tips, mindfulness insights, trail recommendations, and more!