Family-Friendly Hikes in Westchester (and Beyond)


This post is the first in a Hiking the Hudson Valley series for Westchester County Mom. 

When I moved to Westchester, I knew one of the first things I wanted to do was hit the trails. I’ve always loved hiking, and I’m grateful this region offers so much of it! My preschooler and I spent a lot of time finding trails nearby that accommodate his sense of adventure. (Knock any trails with steep drop-offs off the list because my kid thinks climbing them looks fun, and he is fast!).

Since having my second child, I’ve enjoyed exploring new, slightly more challenging trails with baby in tow. Babywearing and hiking steep trails are a great way to burn off the baby weight! 

With all this exploring, I’ve come up with a solid list of trails for families of all ages. Here are some of the best family-friendly hikes in Westchester County (so far, there is still much more to explore).

NOTE: I’ve included a challenge factor for each location, rated 1-5 (1= Great for all ages and abilities; 3 = this trail offers a challenge but could be accomplished with younger children; 5 = leave kids younger than teens at home, you’re in for a real workout!). None of these trails are rated advanced/hard, so you do not need to be a hiking expert to do any of them!

1. Turkey Mountain {Yorktown} Challenge Factor 3

Turkey Mountain is a great hike for kids of most ages. It is steep enough to offer a decent workout for parents but not so challenging that a younger child with decent listening ears couldn’t accomplish the climb. At about two miles, it may take a while with small children, but getting out there counts, not how much of the trail you do, or the time it takes to do it. Despite being okay for younger children, the trail would be best for elementary-age children and older, however (due to length and trail conditions). 
Photo Credit: Author

2. Anthony’s Nose {Cortlandt Manor} Challenge Factor 4

Known for some of the best (if not the best) views in the county, this hike is better for older children, given trail conditions. Some sections of certain trails have steep drop-offs and run right to the edge of cliffs. Other sections are a bit steep or contain water crossings. Overall, the trail is not too challenging, and with two trails to the summit under 2.5 miles, it isn’t too long for a family hike. 
Photo Credit: Erin Kirby
Anthony’s Nose Photo Credit: Erin Kirby

3. Glazier Preserve {Chappaqua} Challenge Factor 1.5  

Looking for a beautiful, easy, short hike perfect for toddlers? Glazier is it! While you can combine trails to create a longer hike, the loop around the pond is short and has lots to see (pond life, bridges, streams, woods, and more). This trail is not stroller friendly, but one is not necessary (unless your child cannot yet walk well, in which case you could bring the stroller and do the boardwalk section located on the left fork as you get into the preserve). 
Glazier Arboretum, Chappaqua [Photo Credit Erin Kirby]
Glazier Arboretum, Chappaqua [Photo Credit Erin Kirby]

4. Rockefeller State Park Preserve {Pleasantville} Challenge Factor 1

Rockefeller is an excellent choice if you need a stroller-friendly, easy, and scenic hike. With a diverse array of trails ranging from wooded to pond, stream, or Hudson River adjacent; farm and field, to hilltop elevations, the carriage trails of Rockefeller are perfect for family members of all ages (we regularly see everyone from newborns to great grandparents on the trails!). Check out the Stone Barns grounds, Glacier Erratic, Rockwood Hall, Swan Lake, and the art gallery while there! This nature preserve is sure to become a family favorite. 
Photo Credit: Erin Kirby Photography

5. Whippoorwill Park {Chappaqua} Challenge Factor 2

Whippoorwill preserve offers similar conditions to Glazier but is slightly more challenging. There is no boardwalk and some bigger hills, making the terrain a bit steeper. The preserve is also larger, and the trails are a bit longer. 

6. Sugarloaf Hill from 9D {Garrison – just outside of Westchester} Challenge Factor 3

Sugarloaf Hill offers scenic Hudson River views without being as challenging as Anthony’s Nose. While there is some steep terrain and a few places with drop-offs, the trail is noticeably easier than its nearby counterpart in the Hudson Highlands. While probably not ideal for very young children, it is manageable for kids just starting elementary school (or perhaps a bit younger if they have some safety awareness). Explore streams, ponds, woods, and fields; catch the gazebo along the way. Plus, you’ll love the views of the Hudson River and West Point. 

Great Local Hiking Resources for Families

  1. Half Pint Hikes in the Hudson Valley
  2. Hiking the Hudson Valley and Beyond 
  3. AllTrails
  4. More Hiking Inspiration from Westchester County Mom: Here, and Here

What’s on my hiking list for the summer?

  1. Mountain Lakes Park
  2. Ward Pound Ridge Reservation 
  3. Catskills Hiking – Overlook Mountain, Plattekill Falls, Huckleberry Point Trail
  4. More Hudson Highlands Trails
Want more insight into great family hiking in the area? You can catch details of my family’s outdoor adventures and get trail inspiration on my new Instagram channel, Mama’s Hiking the Hudson. And stay tuned for more in my Hiking the Hudson Valley series for Westchester County Mom!
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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.