The best family-friendly hikes and walks around Ossining
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Family friendly hiking trails around Ossining offer a diverse landscape on the eastern bank of the Hudson River. The region features a mix of riverfront paths, rolling hills, and dense woodlands. Hikers can explore historic aqueduct paths, extensive nature preserves, and scenic gorge trails. The terrain varies from accessible crushed stone paths to more demanding forest trails with moderate elevation changes.
Best family friendly hiking trails around Ossining
- The most popular family friendly hiking route is Old Croton Aqueduct and…
Last updated: May 12, 2026
23.0km
06:14
320m
320m
Hike the Old Croton Aqueduct and Teatown Lake Loop, a difficult 14.3-mile route combining historic paths with diverse natural scenery.
12.9km
03:29
170m
170m
Hike the moderate 8.0-mile Briarcliff-Peekskill Trailway and Three Lakes Loop in Teatown Lake Reservation, featuring lakes and wildlife.
6
hikers
19.4km
05:12
220m
230m
Hard hike. Very good fitness required. Mostly accessible paths. Sure-footedness required.
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Tips from the Community
Great boardwalk that takes you over the southern edge of Teatown Lake. From it, you get a great view of the water and the surrounding hills. If you are lucky, you may catch a glimpse of some of the wildlife that lives in the pond.
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The Briarcliff Peakskill Trail is a 12-mile hiking trail that runs from Ossining north to Blue Mountain Reservation. This section is a particularly beautiful wooded section. It leads you to Teatown Lake Reservation, a wonderful green area surrounding a large lake.
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Croton Reservoir is one of the three main water supply systems that provide water to New York City.
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Originally built as a primary school in the 1860s, the Crotonville School Building later became the Parker Bale American Legion Post #1590. After closing as a school in 1931, it has served as a meeting place for the largest US wartime veterans service organization, carrying on a rich legacy of community service.
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With construction beginning in 1837, the Old Croton Aqueduct was a response to devastating fires and epidemics in New York City, which lacked adequate clean water. Irish immigrant laborers carried out much of the demanding work. Supplying New York City until 1955, part of the historic Aqueduct reopened in 1987, continuing to provide water to Ossining. However, the Aqueduct's intended capacity quickly proved insufficient for New York's rapidly expanding population. Just a few miles east, the much larger New Croton Aqueduct, engineered by B.S. Church, opened underground in 1890 with triple the capacity, still supplying New York City today.
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Beautiful dam and waterfalls. Nice climb if coming from old quaker bridge
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Enjoy a walk around Teatown Lake and the surrounding preserve. The Briarcliff-Peekskill Trailway bisects the park in the northwest and continues north to Peekskill and south to Ossining. Paid Parking is located at the visitors center on both sides of Spring Valley Road.
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Frequently Asked Questions
How many family-friendly hiking trails are available around Ossining?
There are nearly 100 family-friendly hiking routes around Ossining, with over 50 of them rated as easy, making them perfect for all ages and skill levels.
What makes Ossining a great place for family hiking?
Ossining offers a diverse landscape with riverfront paths, rolling hills, and woodlands, providing a variety of experiences. You'll find historic aqueduct paths, extensive nature preserves like Teatown Lake Reservation, and scenic riverfront trails along the Hudson, ensuring there's something for every family.
Are there any easy, short loop trails suitable for families with young children?
Yes, for an easy and scenic option, consider the 1.9-mile Croton Point Park Loop. It offers picturesque vistas of the Hudson River and is generally flat, making it ideal for families with young children.
What are some unique natural features or landmarks to see on family hikes in Ossining?
Ossining's trails offer several unique sights. You can explore the historic Old Croton Aqueduct paths, or visit the New Croton Dam, a significant landmark. The Tarrytown Reservoir also provides beautiful lakeside views. For a truly distinctive experience, the Sing Sing Kill Greenway offers an ADA-compliant walkway through a gorge.
Are there any stroller-friendly trails in Ossining?
Many sections of the historic Old Croton Aqueduct Trail feature crushed stone carriage roads, which can be suitable for strollers. Additionally, the Sing Sing Kill Greenway is an ADA-compliant concrete walkway, offering a smooth path through a unique gorge setting.
Can I bring my dog on family hikes in Ossining?
Many trails in Ossining are dog-friendly, but it's always best to check specific park or preserve regulations before you go. Generally, dogs are welcome on leash in most public outdoor spaces, including sections of the Old Croton Aqueduct Trail and various nature preserves.
What is the best time of year to go hiking with family in Ossining?
Ossining offers great hiking year-round. Spring and fall provide comfortable temperatures and beautiful scenery, with fall foliage being particularly stunning. Summer offers shaded trails in the woodlands, while winter can be lovely for walks on open trails, though some paths might be icy. Always check conditions before heading out.
Are there any longer, more challenging family-friendly routes for older kids?
For families seeking a longer adventure, the Briarcliff-Peekskill Trailway and Three Lakes Loop is a moderate 8-mile route. Another option is the Old Croton Aqueduct and Teatown Lake Loop, which is a more challenging 14-mile journey combining historical paths with natural beauty.
Where can we find parking for family hikes in Ossining?
Most nature preserves and parks in Ossining, such as Teatown Lake Reservation, Rockefeller State Park Preserve, and Croton Point Park, offer designated parking areas. For trails like the Old Croton Aqueduct, you can often find parking at various access points along its route.
What do other hikers enjoy most about family-friendly trails in Ossining?
The komoot community highly rates the family-friendly trails around Ossining, with an average score of 4.9 stars. Reviewers often praise the diverse landscapes, the historical significance of the aqueduct paths, and the stunning views of the Hudson River. The well-maintained paths and variety of easy options are frequently highlighted as perfect for families.
Are there any trails that offer views of the Hudson River?
Absolutely! Many trails in and around Ossining follow the Hudson River, providing stunning waterfront vistas. Croton Point Park, for example, offers the 1.9-mile Croton Point Park Loop with picturesque views. Crawbuckie Nature Preserve also features long trails with great views of the Hudson River.
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