Family-Friendly Hikes Near Westchester :: The Catskills

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This is the second installment of Westchester County Mom’s Hiking the Hudson Valley feature. You can read the first in the series (and get descriptions of my Family Hike Challenge Factor) here.

The Catskill Mountains may not be in Westchester, but they make for an excellent, family-friendly weekend trip. With fall approaching, it is the perfect time to take a trip to this local mountain range and enjoy some of the many great hikes the Catskills offers!

With all the trails in the Catskills, it probably won’t surprise you that I hardly checked a fraction of the many options off my hiking list this summer; we had a few unexpected issues arise throughout recent months that limited how many trails I could try in the Catskills. That said, I still found time to try many excellent trails. Here is a review of a few that I did get to enjoy!

1. Overlook Mountain Challenge Facto: 4.5

Overlook Mountain is not to be missed, so long as you are physically able to reach the summit, that is! The trail is about five miles round trip, and the first mile is deceptively steep. I thought it was just me who found the first bit tough, but on the hike down, my hiking buddy and I were stopped multiple times by people asking if it got any easier or if they should turn around. It doesn’t help that the path up to the summit is pretty boring. That said, older kids and teens will likely find reaching the summit an attainable goal. The path is not technical, and the summit isn’t too far from the trailhead at about 2.5 miles. Once there, the payoff is huge. An abandoned hotel and fire tower to explore, plus great views, make Overlook Mountain an excellent choice for a family-friendly mountain hike!
 
Photo Credit: Erin Kirby
Photo Credit: Erin Kirby
Photo Credit: Erin Kirby

2. Plattekill Falls Challenge Factor 3.5

Plattekill Falls is a short and beautiful hike, but while the trail is incredibly short, it isn’t a good fit for little feet. The path is narrow, rocky, and steep, with multiple switchbacks. The surrounding landscape includes multiple drop-offs (of several stories) and loose terrain, making it unsafe for very young children. For kids with a good sense of trail safety, this hike is about as good as it gets for the length (.5 miles ROUND TRIP!). 
Photo Credit: Erin Kirby
Photo Credit: Erin Kirby

3. Comeau Property Challenge Factor 1.5

Bring the bathing suits and towels for this 1-mile hike! The trail is incredibly easy (though not stroller accessible, hence the rating of 1.5), and a beautiful stream perfect for wading and swimming passes through at the halfway point that is perfect. Enjoy gorgeous views of Overlook Mountain from the field near the trailhead, walk the well-maintained wooded paths, and end with lunch or ice cream in downtown Woodstock right down the street.
 
Photo Credit: Erin Kirby
Photo Credit: Erin Kirby
Photo Credit: Erin Kirby

4. Kelly Hollow Loop Challenge Factor 2

This trail we hiked last fall, but it is worth including in the list. The trail is easy, though a bit long (3.4 miles) for tiny feet to complete in its entirety. It lacks the views that some of the other trails I’ve reviewed offer, but the beautiful and diverse landscape (streams, woods, a lovely pond, and more) make up for that. It also has a fair bit of elevation gain (AllTrails indicates over 500 feet), though the trail is not so steep that younger kids can’t do it. Plus, the trail gets bonus points for the beautiful drive leading out to the area from the west. Kelly Hollow is an excellent choice if you are in the Margaretville area with your little ones or are just looking for a leisurely hike.
 
Photo Credit: Erin Kirby

5. Windham Path Challenge Factor 1

Windham Path is the perfect trail for all ages. The views will leave adults awestruck, but the trail is easy and stroller friendly. The landscape is varied; fields, forests, streams, bridges, and more occupy this 2.5-mile trail. My preschooler especially enjoyed the story walk along the path; every so often, a new page or two from a picture book appeared on signs, and he was excited to keep going and find out what happened next. While hardly a hike in the adult sense, if you are looking for a trail that your average toddler can accomplish, this is your best bet in the Catskills!
 
 
Photo Credit: Erin Kirby
Photo Credit: Erin Kirby

Want to stay closer to Westchester County? My first article in the Hiking the Hudson series offers excellent options for leaf peeping right in our backyard! You can also follow my hiking adventures on Mama’s Hiking the Hudson for more family-friendly hikes!

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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 (www.themindfullyscientificmama.com), Facebook, Instagram, and Pinterest accounts.

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