4.8
(46)
796
riders
77
rides
Touring cycling routes around Ossining offer a diverse landscape characterized by the Hudson River, rolling hills, and dense woodlands. The region features significant natural and historical elements, including reservoirs and the Old Croton Aqueduct. This terrain provides varied cycling experiences, from challenging climbs to more leisurely, shaded paths.
Last updated: May 16, 2026
5
riders
36.3km
02:28
450m
450m
Hard bike ride. Good fitness required. You may need to push your bike for some segments of this route.
1
riders
34.9km
02:34
360m
360m
Hard bike ride. Good fitness required. You may need to push your bike for some segments of this route.

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1
riders
55.8km
03:36
680m
680m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
riders
24.4km
02:10
210m
210m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
53.0km
03:52
480m
480m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Perched 125 feet high on the bridge path, the Tides of Tarrytown overlook offers a unique perspective on the village's rich history and evolving shoreline. The timber-clad bench doubles as a panoramic viewing platform, allowing you to absorb the northern vista of Tarrytown and the southern skyline of New York City.
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At Painters Point, perched 102 feet high on the Mario M. Cuomo Zee Bridge, find inspiration in the majestic Hudson River scenery. A unique bronze and wood structure frames views of the river and Hook Mountain, inviting reflection and appreciation. Join the long legacy of artists moved by the Hudson's beauty as you stand on this elevated viewpoint.
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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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not really worth seeing at first glance. But then nice houses in the city center. And on the Hudson one expensive residence and one house after another. wow !. On one photo you can see how nice the weather was and how far away NY is (about 60 km)
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Nice old bridge over Croton River. Make sure to dismount if you are on a road bike.
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Beautiful dam and waterfalls. Nice climb if coming from old quaker bridge
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Touring cycling routes around Ossining offer a diverse landscape. You'll encounter rolling hills and dense woodlands, providing both challenging climbs and shaded, picturesque paths. Many routes also feature stunning views of the Hudson River and the New Croton Reservoir.
Yes, Ossining offers a variety of touring cycling routes suitable for different abilities. Out of approximately 77 routes, you'll find about 21 easy routes, 36 moderate routes, and 20 difficult routes, ensuring options for beginners to experienced cyclists.
Many routes in Ossining pass by significant natural and historical features. You can cycle past the impressive New Croton Dam, enjoy views of the Tarrytown Reservoir, or cross the scenic Red Bridge over the Croton Reservoir. The Old Croton Aqueduct Trail itself is a historical landmark offering a unique cycling experience.
For families, the Old Croton Aqueduct Trail offers a relatively flat and scenic path, making it suitable for various skill levels. While specific family-designated routes aren't listed, many of the easy routes, such as the Forest Peaceful Trail loop from Village of Briarcliff Manor, which is 16.3 miles long, provide a pleasant experience through woodlands.
The touring cycling routes in Ossining are highly rated by the komoot community, with an average score of 4.8 stars from over 40 reviews. Cyclists often praise the diverse terrain, the scenic Hudson River views, and the well-maintained paths around the reservoirs and through woodlands.
Yes, many touring cycling routes in Ossining are designed as loops. Popular options include the challenging New Croton Reservoir Loop (22.5 miles) and the Old Croton Aqueduct and Teatown Loop (21.7 miles), which navigates through historical landmarks and varied terrain.
While specific parking areas for each route are not detailed, many parks in Ossining, such as Louis Engel Waterfront Park, offer facilities that may include parking. For routes like the Old Croton Aqueduct Trail or North County Trailway, access points often have designated parking. It's advisable to check specific trailheads for parking availability.
The spring, summer, and fall months generally offer the best conditions for touring cycling in Ossining. These seasons provide pleasant temperatures and vibrant scenery, from blooming spring flowers to colorful autumn foliage. Always check local weather conditions before heading out.
Yes, some major trails like the Old Croton Aqueduct Trail and the North County Trailway have sections that are accessible via public transport, particularly Metro-North Railroad stations in the Hudson Valley. It's recommended to research specific station access points and bike policies for the most convenient travel.
For those seeking longer rides, the New Croton Reservoir Double Loop covers approximately 34.7 miles (55.8 km) with significant elevation gain, offering an extended and challenging experience. The North County Trailway also provides a substantial paved path that connects to other regional trails for longer point-to-point options.
Routes offering views of the Hudson River, such as those near Louis Engel Waterfront Park, are highly scenic. The New Croton Reservoir Loop is also celebrated for its beautiful reservoir vistas. Additionally, routes through dense woodlands, like the Forest Peaceful Trail loop from Village of Briarcliff Manor, provide a tranquil and picturesque experience.
For a moderate touring cycling experience, consider the North County Trailway – The Pine Bridge Monument loop from Village of Briarcliff Manor. This 18.4-mile (29.6 km) route offers a balanced ride with some elevation changes, passing by Revolutionary War monuments and an old railway depot.


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