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Routes
Road cycling routes
United States
New York
Westchester County

Ossining

The best road cycling routes around Ossining

4.2

(33)

1,525

riders

91

rides

Road cycling routes around Ossining, New York, offer diverse landscapes for cyclists. The region is characterized by its location along the Hudson River, providing waterfront vistas, and features the New Croton Reservoir and Dam. Terrain includes well-paved multi-use trails and local road networks with varying elevation gains. These physical features contribute to a range of cycling experiences, from gentle rides to more challenging climbs.

Best road cycling routes around Ossining

  • The most popular road cycling route is North County Trailway…

Last updated: April 28, 2026

6

riders

#1.

North County Trailway and Croton Reservoir Loop

59.2km

03:08

690m

690m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Tips from the Community

Lisa
June 23, 2025, Trailside Café

A great place to stop for a snack and a quick drink.

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Pandian
June 7, 2025, New Croton Dam

Careful when you ride on these road lots of potholes.

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Lisa
September 26, 2024, Rockland Lake South

This 256-acre lake might seem pretty shrimpy alongside the mighty Hudson River to the east, but the lake has a nice road-ride loop all the way around it, and a small jetty leading into the water.

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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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This bronze statue is a memorial to the Battle of Pines Bridge, a battle in the Revolutionary War. The monument is made to reflect the diversity of the soldiers in the war. The monument is located in Railroad Park, which has benches and a cafe.

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There are great views over the water in either direction as you ride along Croton Lake Road. The elevated position of the bridge gives you a lovely vantage point and a wonderful photo opportunity.

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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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Felix
December 30, 2022, New Croton Dam

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

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Frequently Asked Questions

How many road cycling routes are available around Ossining?

There are nearly 100 road cycling routes around Ossining listed on komoot. These routes cater to various skill levels, with 21 easy, 61 moderate, and 16 difficult options available.

What types of terrain can I expect on road cycling routes in Ossining?

Ossining offers a diverse range of terrain for road cyclists. You'll find well-paved multi-use trails like the North County Trailway and South County Trailway, as well as local road networks. Routes vary from flat, easy rides to those with significant elevation gains, especially around the New Croton Reservoir area.

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

Yes, Ossining has several family-friendly options, particularly on its extensive multi-use trail network. Routes like the North County Trailway loop from Village of Briarcliff Manor offer mostly well-paved, easy surfaces suitable for a pleasant ride with family members. Many of the 21 easy routes available are great for beginners or those looking for a relaxed pace.

What scenic landmarks or natural features can I see while cycling in Ossining?

Road cycling routes in Ossining offer stunning views of the Hudson River and the Palisades. You can also cycle past the impressive New Croton Dam and the New Croton Reservoir. Other notable natural features include the Tarrytown Reservoir and the Red Bridge over the Croton Reservoir, providing picturesque backdrops for your ride.

Are there any challenging road cycling routes for experienced riders?

Absolutely. For experienced riders seeking a challenge, Ossining offers routes with significant elevation gains. The North County Trailway and Croton Reservoir Loop, for example, is a moderate route covering 36.8 miles with over 2,200 feet of elevation gain. There are 16 difficult routes available for those looking for more demanding climbs and longer distances.

What do other cyclists say about road cycling in Ossining?

The road cycling routes in Ossining are highly rated by the komoot community, with an average score of 4.5 stars from over 40 reviews. Cyclists often praise the diverse landscapes, the well-maintained multi-use trails, and the scenic views of the Hudson River and New Croton Reservoir.

Are there any loop road cycling trails in the Ossining area?

Yes, many road cycling routes in Ossining are designed as loops, allowing you to start and end at the same point. Examples include the New Croton Dam – New Croton Dam loop from Westchester County and the Teatown Lake Boardwalk – The Pine Bridge Monument loop from Westchester County, offering convenient circular rides.

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

Ossining is accessible via Metro-North Railroad, which has a station in the village. While specific routes may require a short ride from the station, the presence of public transport makes it feasible to bring your bike and access the area's cycling network. Always check train schedules and bike policies before planning your trip.

Where can I find parking for road cycling trails in Ossining?

Many parks and trailheads in Ossining and the surrounding Westchester County area offer dedicated parking facilities. For instance, Croton Gorge Park provides parking for accessing the New Croton Dam area, and various points along the North and South County Trailways have parking lots. It's advisable to check specific route starting points for parking availability.

What is the best time of year for road biking in Ossining?

The spring, summer, and fall months generally offer the best conditions for road biking in Ossining, with pleasant temperatures and vibrant scenery. Autumn, in particular, provides beautiful foliage along many routes. While some dedicated trails may be accessible in winter, local road networks can be affected by snow and ice, so always check weather conditions.

Are there any trails that combine historical interest with road cycling?

Yes, the Old Croton Aqueduct Trail, while not exclusively a road cycling path, offers a unique historical experience. It roughly follows the route of the historic aqueduct, providing a journey through nature and history. Sections of this trail are suitable for road bikes, though some parts may be unpaved.

What are some notable multi-use trails for road cycling in the area?

Ossining is well-connected to several popular multi-use trails ideal for road cycling. These include the North County Trailway, known for its well-paved surfaces, the South County Trailway, and the Briarcliff-Peekskill Trailway, which extends north towards Blue Mountain Reservation. These trails offer smooth riding and connect to various scenic points.

Most popular routes around Ossining

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