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United States
New York
Westchester County

Ossining

The best cycling routes around Ossining

4.8

(49)

870

riders

78

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.

Best touring cycling routes around Ossining

  • The most popular touring cycling route is New Croton Reservoir Loop, a 22.5 miles (36.3 km) trail that takes 2 hours 27 minutes to complete.…

Last updated: April 30, 2026

5

riders

#1.

New Croton Reservoir Loop

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.

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Hard

1

riders

Hard bike ride. Good fitness required. You may need to push your bike for some segments of this route.

Hard
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1

riders

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Tips from the Community

Pandian
June 7, 2025, New Croton Dam

Careful when you ride on these road lots of potholes.

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oliviakellis
September 12, 2023, New Croton Dam

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)

Translated by Google

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Felix
December 30, 2022, Old Quaker Bridge

Nice old bridge over Croton River. Make sure to dismount if you are on a road bike.

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Felix
December 30, 2022, New Croton Dam

Beautiful dam and waterfalls. Nice climb if coming from old quaker bridge

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Felix
November 13, 2022, North County Trailway

Nice long trail on old train track route.

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Great views of Croton reservoir and the red bridge itself is worth a stop. That said watch out for stopped cyclist and pedestrians if you're biking through.

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Joseph
July 19, 2022, New Croton Dam

The New Croton Dam forms the New Croton Reservoir, part of the New York City water supply system. Construction began in 1892 and was completed in 1906. The dam is 266 feet broad at its base and 297 feet high from base to crest. At the time of its completion, it was the tallest dam in the world. Croton Gorge Park offers views of the dam from directly downstream. The Old Croton Trail, a popular hiking and biking path that roughly follows the route of the Old Croton Aqueduct, has an endpoint near the base of the dam. Teatown Lake Reservation, a nature preserve, lies nearby as does Croton Point Park in Croton-on-Hudson.

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Frequently Asked Questions

What kind of terrain can I expect on touring cycling routes around Ossining?

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.

Are there touring cycling routes for all skill levels in Ossining?

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.

What are some notable landmarks or attractions I can see along touring cycling routes in Ossining?

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.

Are there any family-friendly touring cycling routes in Ossining?

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.

What do other touring cyclists enjoy most about cycling in Ossining?

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.

Are there any circular touring cycling routes around Ossining?

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.

Where can I find parking for touring cycling routes in Ossining?

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.

What is the best time of year to go touring cycling in Ossining?

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.

Can I access touring cycling routes in Ossining using public transport?

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.

Are there any long-distance touring cycling routes in the Ossining area?

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.

What are some of the most scenic touring cycling routes in Ossining?

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.

Are there any specific trails that are particularly good for a moderate touring cycling 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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