The best walks and hikes around Ossining
4.9
(55)
974
hikers
115
hikes
Hiking around Ossining, New York, is characterized by a mix of riverfront paths, rolling hills, and dense woodlands. The area sits on the eastern bank of the Hudson River, offering routes that follow historic aqueducts and wind through large nature preserves. The terrain varies from crushed stone carriage roads to more challenging forest trails with moderate elevation changes. Ossining's landscape provides diverse options for outdoor activities, particularly hiking, with scenic Hudson River views and numerous parks.
Best hiking trails around Ossining
- The most popular hiking route is Croton Point Park Loop, an easy 1.9 miles (3.1 km) trail that takes about 48 minutes to complete. This route offers scenic Hudson River views and explores a unique peninsula.
- Another top favourite among local hikers is Croton RiverWalk, a moderate 6.9 miles (11.1 km) path. This trail follows the Croton River, providing a mix of natural scenery and riverside access.
- Local hikers also love the North County Trailway, an 8.6 miles (13.9 km) trail leading through varied landscapes, often completed in about 3 hours 36 minutes.
- Hiking around Ossining is defined by historic aqueduct paths, large nature preserves, and trails along the Hudson River. The network of routes provides options for different ability levels, from easy walks to longer, more difficult hikes.
- The routes in Ossining are highly rated by the komoot community with an average score of 4.9 stars from over 50 reviews. More than 900 hikers have used komoot to explore Ossining's varied terrain.
Last updated: April 26, 2026
3.09km
00:48
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
23.0km
06:14
320m
320m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
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3
hikers
11.1km
02:52
50m
50m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
3
hikers
13.9km
03:36
90m
90m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
12.9km
03:29
170m
170m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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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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The memorial is a giant sundial from steel salvaged from the World Trade Center site. There are several plaques on the memorial to remember the planes that crashed, the first responders, and some messages of hope for the future.
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Croton Point Park is a popular park on Croton Bay. The park has a lot to offer, including hiking trails, a pavilion, a playground, and a beach.
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As you cross over an old rail trestle bridge, you are treated to great views of the New Croton Reservoir. The bridge is not open for car traffic, so you can stop on the path for a quick break to take in the views.
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Interesting tunnel under Kitchawan Road. The tunnel was constructed when this trail was still a railroad, but it has been adapted for hikers and cyclists. It is a fairly short tunnel, so you are able to walk through it without a light.
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The North County Trailway is a 20-mile rail trail from Baldwin Place to Sleepy Hollow. The section around Millwood passes several Revolutionary War monuments, and goes through Echo Lake State Park. The trail is slightly downhill if you are going north to south.
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Frequently Asked Questions
Are there many hiking trails to choose from around Ossining?
Yes, there's a wide variety of trails. You can find nearly 90 different routes in the area, ranging from easy lakeside strolls to more demanding woodland hikes.
What do other hikers enjoy most about the trails in Ossining?
The area is highly rated by the komoot community, with an average score of 4.9 stars. Hikers often praise the mix of historic paths, like the Old Croton Aqueduct, and the serene, well-maintained trails within large nature preserves.
Are there any dog-friendly hiking trails in the Ossining area?
Many parks in the region are dog-friendly, but policies often require dogs to be on a leash. Kitchawan Preserve is a popular spot for hiking with dogs, offering rustic trails through woodlands and fields. Always check the specific park's regulations before you go.
Can I find any easy, beginner-friendly hikes near Ossining?
Absolutely. The region has over 50 easy-rated walks. A great option is Rockefeller State Park Preserve, which features an extensive network of wide, crushed-stone carriage roads that are perfect for a gentle hike, such as the paths around the scenic Swan Lake.
Are there any hikes with good views of the Hudson River?
Yes, several trails offer rewarding views. Crawbuckie Nature Preserve provides an intimate hiking experience with several observation platforms looking out over the Hudson. For more panoramic vistas, the Eagle Hill Trail in Rockefeller State Park Preserve rewards climbers with expansive views of the Hudson River Valley.
What are some good options for a family-friendly walk?
Teatown Lake Reservation is an excellent choice for families. It's a highly-regarded 1,000-acre preserve with a nature center and 15 miles of trails, including an easy Lakeside Loop that features a floating bridge, which is often a hit with kids.
Can I get to any trailheads using public transport?
Yes, Ossining's train station provides great access to the trail network. For a challenging day out, you can take on the Ossining Train Station to New Croton Dam loop, which starts and ends right at the station.
Are there any long circular hikes in the area?
For those seeking a longer trek, the Teatown Lake Reservation loop via Briarcliff Peakskill Trail is a great moderate option. This 8-mile (12.9 km) circuit explores the diverse habitats of the reservation, from forests to lakeside paths.
What is the Old Croton Aqueduct Trail like?
The Old Croton Aqueduct Trail is a unique, relatively flat linear park that follows the path of a 19th-century aqueduct. The section near Ossining is a mix of wooded paths and village walkways, offering a hike rich in history. For more information on the history and access points, you can check visitsleepyhollow.com.
Where can I find a hike along the waterfront?
For a pleasant walk with river views, the Croton Point Park to Croton Landing Park route is a fantastic choice. This moderate trail offers a scenic path along the Hudson, connecting two popular local parks.
Are there any paved or rail trails for walking?
Yes, the North County Trailway near Millwood is a multi-use path that's great for a straightforward walk. It provides a smooth, mostly flat surface suitable for all fitness levels.
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