guides

Family Hikes Armonk, Chappaqua, Mount Kisco, Pleasantville

Trails for all ages in our area of Westchester County and slightly beyond

By Kelly Fitzpatrick November 9, 2022

What feels more like fall than a hike in the foliage?  Whether you are looking for a stroller friendly trail or have advanced teen hikers, MacaroniKID Armonk – Chappaqua – Mount Kisco – Pleasantville has you covered for a round-up of the best hikes in and around our area.


Hikes with Littles:

Bear Mountain Zoo: This paved trail works well with a stroller and has enough to do and see for kids of all ages.  It’s even a nice place to go on a date!  Admission to the zoo is donation based – look for the box at the entrance.  Native animals that have been injured or are unable to survive on their own in the wild have been rehomed here and there are also indoor exhibitions and interactive displays.  This walk in the woods features signposts identifying local fauna and area history.  It’s an easy 1.5-mile loop walk with minimal elevation.

Location: 98 Hessian Lake Drive, Bear Mountain, NY 10911.


Croton Gorge Park: One of my favorite places to go in the winter for sledding and snow play, Croton Dam is also a great place for a fall hike.  The stroller friendly out and back walk offers phenomenal views of the reservoir.  The cascading water at the bottom is nothing short of mesmerizing – the sheer size of it alone is captivating.  Add a playground, picnic tables, and bathroom facilities and you’ve got a great day out.  The walk is roughly a mile and a quarter with options to add on.  Parking can be a challenge on a fall weekend, but it’s the kind of hike you can do in the early evening after work or anytime of year.  

Location: Route 129, Cortlandt, NY  10566  

 - 35 Yorktown Rd, Croton-on-Hudson, NY 10520 using online maps  


Muscoot Farm: A hiking guide for little people would not be complete without the addition of Muscoot Farm.  While the trails can be muddy, they are usually stroller friendly, and you can once again visit with animals along the way.  Take a slow stroll and absorb the surroundings – there’s often something that will surprise you, no matter how many times you have visited.  We love to wear our rainboots and jump in the puddles.It is an all weather kind of place.  There are over 7 miles of hiking trails so you could really go with any age group.  In our house it’s most known with the small people, but you’ll see hikers of all ages once you venture past the stables.  Bathrooms available.

Location: 51 Rte 100, Katonah 10536


Gedney Park: Parts are stroller-friendly and parts can make a toddler feel like an explorer in the woods.  Add in two playgrounds, bathrooms, picnic tables, a pond, and Chappaqua Library’s Story Walk and you’ve got it made. Super dog friendly and a staple in the area.  The outer loop is 1.7 miles.

161 Millwood Road, Chappaqua 10514


Hikes with Kids and Tweens:

Turkey MountainTurkey Mountain offers a 2.1 mile loop trail with enough elevation to be strenuous at points.  If you are not huffing by the time you summit, the views will surely take your breath away.  On a clear day you’ll see the Croton Reservoir and dam, the Hudson River; New York City, Bear Mountain, the Hudson Highlands, and even the Shawangunks.  Give yourself an hour at a moderate pace and two for conversation and rest.  Leave the stroller at home!

Location: (From their website) Off the west side of Route 118, approximately 2 mile south of the intersection of Routes 202, 35, and 118, and one mile north of the intersection of Route 129 and 118, opposite of Croton Heights Road.


Kensico Dam PlazaThis hike is short, yet steep, and offers beautiful views of the reservoir.  You can walk up the height of the dam on stairs or just alongside of them.  I’ve done it with the baby in a carrier and with my three-year-old, but it depends on your comfort level.  The walk along the top of the reservoir is a simple stroll and well worth the climb.  I recommend walking up on the left side and down on the right as the left side is much steeper on the descent.  Fun fact - my son calls it the castle and your littles will too if you make it that kind of adventure!

Location: 1 Bronx River Parkway, Valhalla 10595


Westmoreland Sanctuary: Donations accepted.  Easy parking and restrooms available.  Not stroller friendly, however we did this hike with a baby in a carrier, a toddler who walked the entire time, and a tween and it was a hit for everyone.You’ll see marsh views, protected areas, a fern forest, a whimsical playhouse, informational signs and a butterfly garden.  It’s a choose your own adventure of trails – there’s over 8 miles in total.  Low elevation and quite scenic.  

Location: 260 Chestnut Ridge Road, Mount Kisco 10549


Hikes with Teens and Adults:

Torne Loop: This Highland Falls hike may only be a mile loop, but it includes more than one strenuous scramble.  You'll follow a steep incline for much of the walk and need to be cautious about watching the markers.  Two spots require the use of a rope (already there) and this hike should be done with others.  The 360-degree views of the Hudson River, West Point, and Bear Mountain Bridge at the top are worth the climb, as is the monument to fallen soldiers created by visitors.  It's a quiet spot for reflection, gratitude, and rest.

Location: 288 Mine Road, Highland Falls, 10928

Breakneck Ridge Loop: This steep and strenuous hike is one of the most popular in the Hudson Valley for skilled trekkers.  Cars park along 9D year-round on the weekends for this trail, although it is best to do on a mild weathered weekday to avoid the crowds as well as any slips or falls when the rocks are wet.  Suitable footwear is a must, as is a comfort level with near vertical hiking.  The views are breathtaking and serve as sweet rewards for your efforts.

Location: 1 Route 9D, Beacon, 12508



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