Family Hikes Near Westchester County :: The Hudson Highlands


Views from hiking the Hudson Valley.Since my last hiking guide was published last year, I’ve continued exploring and hiking throughout Westchester County and beyond. We are fortunate to live in an area with an excess of amazing trails, and I feel like there is an endless supply of hidden corners to discover in the region.

This article is dedicated to my favorite area for local hikes at the moment: The Hudson Highlands.

Several trails in the region were discussed in a previous guide, so I won’t mention them here. That guide also contains information about my Hiking Challenge Factors, a scale from 1 to 5, which specifies the difficulty for families (rather than your average hiker), including whether the trail is stroller-friendly. But for those looking for more options, here are five more awesome trails the entire family will enjoy!

1. Cornish Estate Trail Challenge Factor 2

Featuring the ruins of a beautiful estate, easy (and partially paved) trails, and views of the Hudson River, this popular hike is sure to be a hit with the entire family! Be sure to get there early on weekends; there is limited parking, and the lot is used by hikers on multiple popular trails.

2. South Beacon Mountain via Casino Trail Challenge Factor 5

Mt. Beacon is the tallest of the highland mountains, and the views make the long set of stairs at the beginning of the hike completely worth it. From the foundation of the old casino (all that is left of the building itself), you can glimpse Mohonk (including the famous tower), the Shawangunk Ridge, and the Catskills. The hike is steep, contains some drop-offs, and is more than three miles, making it best suited for older kids.

I’ve read reports of kids as young as five conquering the mountain. Extend the hike by heading to the fire tower and North Mt. Beacon (the highest peak in the highlands). Like the Cornish Estate trailhead, you’ll want to arrive early. Parking is at a premium! Alternatively, park near the train station or in town and catch the free shuttle bus.

3. Dennings Point via Madam Brett Park Challenge Factor 2 (keep it to the first bit for 1 to 1.5)

Looking for a more accessible trail in Beacon? Set at sea level instead of over a thousand feet up, Dennings Point is a beautiful riverfront destination. While the trail is a bit long for the smallest feet, if you decide to do the entire thing (about 3 miles), it is well worth the trip! Portions of the trail are stroller-friendly, but the further out you get, the trail ceases to be so. Once you reach the end, you’ll find rocky beaches with unparalleled views of the highlands.

4. Bull Hill from Nelsonville Challenge Factor 5

While its neighbor Breakneck Ridge gets all the attention, Bull Hill is taller and technically a mountain with its summit at over 1400 feet! A few trails traverse the peak, but the short loop from Nelsonville is the quickest route. The hike is less challenging than Breakneck but still best for older kids; the hike can get steep, and depending on direction, you may face a mini rock scramble or two. Check out some of the beautiful views here.

5. School Mountain Trail, Fahnestock Trail, Round Hill Bypass Trail Loop Challenge Factor 4 (keep it to the first portion for 1.5)

Maybe I shouldn’t share this (I might be letting you in on a secret and inadvertently making the trails more busy and harder to navigate for myself), but Fahnestock State Park is a hidden gem. The summits contain views you’d never believe are mere minutes from the Westchester County line, and the hikes range from easy to moderately difficult. The trail loop mentioned here is great for families with slightly older kids. Still, the beginning is perfect for even the littlest feet and contains bridges, water views, and glimpses of various animals. Check out this clip for some of the great features on this trail. 

6. Notable mention from a previous guide: Anthony’s Nose

Head over to that guide to read more! Or, check out this clip for some of the stunning views during the middle of the winter after a big snowstorm!

Are you new to hiking? Please read the first guide in the Hiking the Hudson Valley series, and check out my hiking tips for families here!

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Erin is the mother of one sweet, rambunctious toddler and wife to a talented chef. Professionally, she is a former special educator and preschool teacher, and is currently a cognitive neuroscience researcher and Ph.D candidate in Cognitive Science in Education with specializations in neuroscience, cognitive development, and neurodiversity/autism. She holds masters degrees in cognitive science, and neuroscience in education, from Teachers College, Columbia University, and undergraduate degrees in special education (with an additional concentration in elementary education and a minor in English) and early childhood education. As the wife of a chef, food is a huge part of her family culture, and she enjoy both cooking and baking. Some of her other hobbies include hiking, traveling, jogging, meditation, animal rescue, playing piano and guitar, crafting, reading, and of course, writing. You can follow her parenting journey and pick up tips on great kids activities here on Westchester Moms Blog, as well as her website (, Facebook, Instagram, and Pinterest accounts.



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