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Routes
Gravel rides
United States
New York
Westchester County

Ossining

The best gravel rides around Ossining

4.6

(14)

43

riders

8

rides

Gravel biking around Ossining offers diverse landscapes, extensive trail networks, and notable natural features. The region is characterized by riverfront access, historic pathways, and wooded areas, providing varied scenic and challenging routes. Topography includes hills and valleys, offering elevation changes that add to the dynamic riding experience. These features make Ossining a compelling destination for gravel biking enthusiasts.

Best gravel bike trails around Ossining

  • The most popular gravel bike trail is Old Croton Aqueduct Trail – Tarrytown Highlights loop from Croton-Harmon, a 31.6 miles (50.8 km) trail that takes 4 hours 7 minutes to complete. This difficult route follows a historic pathway offering varied terrain and scenic views.
  • Another top favourite among local gravel bikers is Old Erie Rail Trail (gravel) – Piermont Railway Station (historic) loop from Tarrytown, a moderate 24.0 miles (38.7 km) path. This route features gravel sections and includes mostly paved surfaces, suitable for various skill levels.
  • Local gravel bikers also love the New Croton Dam – Old Croton Dam Road Bridge loop from Croton-Harmon, a 16.5 miles (26.5 km) trail leading through river valleys and past historic structures, often completed in about 1 hour 30 minutes.
  • Gravel biking around Ossining is defined by the Hudson River, the Old Croton Aqueduct, and extensive wooded areas. The network offers options for different ability levels, from moderate paths to more challenging routes with significant elevation gain.
  • The routes in Ossining are highly rated by the komoot community with an average score of 4.5 stars from more than 10 reviews. More than 50 gravel bikers have used komoot to explore Ossining's varied terrain.

Last updated: April 30, 2026

3.9

(10)

16

riders

#1.

Old Erie Rail Trail (gravel) – Piermont Railway Station (historic) loop from Nyack

34.1km

02:08

210m

210m

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

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Moderate

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

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

Hard

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

Moderate

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

Hard
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Popular around Ossining

Hiking around Ossining

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Tips from the Community

Hans
April 19, 2026, Van Cortlandt Greenway

one of the many great bike paths in New York (State) leads directly north. Paved and mostly through forest, it's great to ride. Super to use for a longer round.

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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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A great trail, although ride with caution and a sturdy bike

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Great trail and only occasional crossing traffic

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Wonderful gravel path along the Hudson

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This is a beautiful section of the North County Trail that runs between Elmsford to Tarrytown Lakes. At the north end of this section, the trail intersects with Tarrytown Lakes Extension Trail, a paved path with takes you along the banks of Tarrytown Reservoir.

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Lisa
September 26, 2024, Haverstraw River Trail

You can enjoy almost five miles of biking along the river on this pretty, though sometimes narrow, trail. Watch out for other trail users, and please don't try this on skinny bike tires; there are parts where some riders might rather have a mountain bike, or at least a gravel bike.

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Lisa
September 25, 2024, New Croton Reservoir

This massive reservoir is about nine miles long, stretching through five different towns. There's a gorgeous, cascading spillway on the west of the reservoir. In this particular spot, you can access the shore of the reservoir just off Croton Lake Road, or via the Teatown-Kitchawan Trail.

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Frequently Asked Questions

How many gravel bike trails are available around Ossining?

Ossining and its surroundings offer a good selection of gravel biking routes. There are 11 distinct gravel bike trails available, catering to various skill levels from moderate to difficult.

What are the general difficulty levels of gravel biking in Ossining?

The gravel biking routes around Ossining offer a mix of challenges. You'll find 3 easy routes, 4 moderate routes, and 4 difficult routes, ensuring options for different experience levels. Routes like the Old Croton Aqueduct Trail – Tarrytown Highlights loop from Croton-Harmon are considered difficult, while the Old Erie Rail Trail (gravel) – Piermont Railway Station (historic) loop from Tarrytown is a moderate option.

What do other gravel bikers say about the trails in Ossining?

The gravel biking experience in Ossining is highly regarded by the komoot community, with an average rating of 4.5 out of 5 stars from 13 reviews. Riders often praise the diverse landscapes, historic pathways, and varied terrain that make for a dynamic riding experience.

Are there any circular gravel bike routes in Ossining?

Yes, many of the gravel bike routes in Ossining are designed as loops, allowing you to start and end at the same point. Examples include the Old Erie Rail Trail (gravel) – Piermont Railway Station (historic) loop from Village of Nyack and the New Croton Dam – Old Croton Dam Road Bridge loop from Croton-Harmon.

What kind of terrain can I expect on gravel bike trails in Ossining?

Gravel biking in Ossining offers a diverse range of terrain. You can expect a mix of dedicated gravel trails like sections of the Old Croton Aqueduct and Old Erie Rail Trail, as well as local dirt and gravel roads. The region's topography includes hills and valleys, providing varied elevation changes and a dynamic riding experience. Some routes may feature loose gravel, packed dirt, and even some ruts, making it ideal for gravel bikes.

What natural features or landmarks can I see while gravel biking near Ossining?

Ossining's gravel routes often pass by significant natural and historical features. You can enjoy stunning views of the Hudson River and Croton River. Many trails, like the Old Croton Aqueduct Trail, follow historic pathways. Other notable sights include the New Croton Dam, Tarrytown Reservoir, and the Red Bridge over the Croton Reservoir. The region also boasts extensive parkland and natural conservation areas like Teatown Lake Reservation.

Are there any historical sites accessible by gravel bike in Ossining?

Absolutely. The Old Croton Aqueduct Trail is a historically significant landmark listed on the National Register of Historic Places, offering a peaceful path through nature and history. You can also explore routes that pass by the New Croton Dam and other historic structures, such as the New Croton Dam – Old Croton Dam Road Bridge loop from Croton-Harmon.

Is it possible to reach the gravel trails using public transport?

Yes, several gravel routes in the Ossining area are accessible via public transport. For instance, the Old Croton Aqueduct Trail – Tarrytown Highlights loop starts from Croton-Harmon, which is a Metro-North train station. Similarly, routes originating from Tarrytown or Nyack are often convenient for public transport users.

Where can I find parking for gravel bike trails near Ossining?

Parking is generally available near trailheads and in various parks throughout Ossining and the surrounding areas. Many routes, especially those starting from towns like Tarrytown, Croton-Harmon, or Nyack, will have designated parking areas. For specific park information, you can check the Town of Ossining Recreation and Parks website.

Are there family-friendly gravel biking options in Ossining?

While some routes are more challenging, there are options suitable for families, especially those with some biking experience. The Old Erie Rail Trail, for example, includes mostly paved surfaces and gravel sections that are suitable for various skill levels. When planning a family outing, look for routes described as 'easy' or 'moderate' and consider their distance and elevation gain.

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

The best time for gravel biking in Ossining is typically during the spring, summer, and fall months. Spring offers lush greenery, while fall provides stunning foliage. Summers are generally pleasant, though it's always wise to check the weather forecast. Winter riding is possible, but conditions can be variable with snow and ice, making some trails less accessible or more challenging.

Can I bring my dog on the gravel bike trails in Ossining?

Many trails and parks in the Ossining area are dog-friendly, but it's essential to check specific regulations for each trail or park. Generally, dogs are welcome on leash on most public trails. For example, the Town of Ossining maintains over 130 acres of parkland, some of which include dog parks and nature trails where leashed dogs are permitted. Always ensure your dog is under control and that you clean up after them.

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