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.
Last updated: April 28, 2026
6
riders
59.2km
03:08
690m
690m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
21
riders
61.4km
02:38
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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18
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
7
riders
26.9km
01:20
330m
330m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
6
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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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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Croton Reservoir is one of the three main water supply systems that provide water to New York City.
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Beautiful dam and waterfalls. Nice climb if coming from old quaker bridge
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.


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