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Gravel rides
United States
New York
Westchester County

Sleepy Hollow

The best gravel rides around Sleepy Hollow

4.2

(27)

108

riders

12

rides

Gravel biking around Sleepy Hollow, New York, offers diverse terrain shaped by the Hudson River Valley and its surrounding landscapes. The region features rolling hills, dense forests, and historic pathways like the Old Croton Aqueduct Trail. These natural features provide varied routes for gravel cyclists, from riverside paths to more challenging climbs. The area's geography supports a range of gravel biking experiences, incorporating both natural beauty and historical elements.

Best gravel bike trails around Sleepy Hollow

  • The most popular gravel…

Last updated: June 28, 2026

4.0

(8)

24

riders

#1.

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

41.4km

02:39

270m

270m

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

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Moderate

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

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

Hard

Hard gravel ride. Very 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
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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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Jamie S.
September 3, 2024, Nyack River Trail

Nyack Beach State Park features a flat, two-mile multi-use path along the Hudson River, which is also part of the Hudson River Valley Greenway. The Nyack River Trail offers scenic views with the river on one side and the towering Palisades cliffs on the other. It is open for biking, walking, fishing, and cross-country skiing in the winter. The park is part of a larger network of parks including Rockland Lake, Hook Mountain, and Haverstraw Beach State Parks.

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Frequently Asked Questions

How many gravel bike trails are available around Sleepy Hollow?

There are over 15 gravel bike trails available around Sleepy Hollow, offering a variety of experiences for different skill levels. The komoot community has explored nearly 100 of these routes.

What kind of terrain can I expect on gravel bike trails around Sleepy Hollow?

The terrain around Sleepy Hollow is quite varied, shaped by the Hudson River Valley. You can expect a mix of rolling hills, dense forests, and historic pathways. Routes often feature sections along the Hudson River, tranquil valleys like the Pocantico, and the extensive carriage trails of Rockefeller State Park Preserve.

Are there gravel bike trails suitable for beginners in Sleepy Hollow?

Yes, there are several easier gravel bike routes. While specific beginner routes aren't detailed, the region offers paths with fewer elevation changes, particularly along sections of the Old Croton Aqueduct Trail. For a moderate option, consider the Old Erie Rail Trail (gravel) – Piermont Railway Station (historic) loop from Village of Nyack, which is 21.2 miles long.

Are there challenging gravel bike routes for experienced riders?

Absolutely. For experienced riders seeking a challenge, routes like the Old Croton Aqueduct Trail – Old Croton Dam Road Bridge loop from Irvington offer a difficult 39.1-mile path with varied scenery and significant elevation changes. Another demanding option is the New Croton Dam – Old Croton Aqueduct Trail loop from Blauvelt State Park, covering over 61 kilometers.

Can I find circular gravel bike routes in the area?

Yes, many of the gravel bike trails around Sleepy Hollow are designed as loops. Examples include the Piermont Railway Station (historic) – Old Erie Rail Trail (gravel) loop from Tappan, a 19.1-mile route, and the Old Erie Rail Trail (gravel) – Piermont Railway Station (historic) loop from Tarrytown, which is 38.6 kilometers long.

What scenic viewpoints or natural features can I see along the gravel bike trails?

Gravel biking in Sleepy Hollow offers stunning views of the Hudson River, including the Tappan Zee Bridge (Governor Mario M. Cuomo Bridge) and the Palisades. You can also explore tranquil water bodies like Tarrytown Lakes and the Kensico Reservoir. Many routes traverse rolling hills and dense forests, especially within areas like Rockefeller State Park Preserve.

Are there any historic sites or attractions accessible by gravel bike?

Yes, the region is rich in history. The Old Croton Aqueduct Trail is a historic pathway that many gravel routes incorporate. You can also explore the unique landscape of Sleepy Hollow Cemetery or visit Kingsland Point Park for views of the Hudson River. For more information on local attractions, you can visit visitsleepyhollow.com.

Where can I park when gravel biking in Sleepy Hollow?

Parking is generally available near popular trailheads and parks. For example, areas around the Old Croton Aqueduct Trail and Rockefeller State Park Preserve often have designated parking facilities. It's advisable to check specific starting points for routes on komoot for detailed parking information.

Are there any cafes or places to stop for refreshments along the routes?

Yes, you'll find options for refreshments. The 9W Market is a popular stop for cyclists. Many routes pass through or near towns like Tarrytown and Nyack, where you can find various cafes and eateries to refuel during your ride.

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

The best time for gravel biking in Sleepy Hollow is typically spring, summer, and fall. These seasons offer pleasant temperatures and vibrant scenery, from spring blooms to autumn foliage. While winter biking is possible, trail conditions can vary due to snow and ice, so checking local conditions is recommended.

Are the gravel bike trails in Sleepy Hollow family-friendly?

Many sections of the gravel bike trails, particularly those with less elevation gain like parts of the Old Croton Aqueduct Trail, can be suitable for families. Rockefeller State Park Preserve also offers extensive carriage trails that are generally well-maintained and provide a pleasant environment for family rides. Always check the route's difficulty and length on komoot to ensure it matches your family's abilities.

What do other gravel bikers enjoy most about gravel biking in Sleepy Hollow?

The gravel biking experience in Sleepy Hollow is highly rated by the komoot community, with an average score of 4.2 stars from over 10 reviews. Riders often praise the diverse terrain, the stunning Hudson River views, and the unique blend of natural beauty with historic aqueduct trails. The variety of routes, from moderate loops to more challenging paths, is also frequently highlighted.

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