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Gravel rides
United States
New York
Westchester County

Pleasantville

The best gravel rides around Pleasantville

5.0

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46

riders

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rides

Gravel biking around Pleasantville offers a diverse landscape characterized by former rail trails, scenic greenways, and routes around significant reservoirs and dams. The region features varied terrain, including paths along historic railway lines, paved and unpaved sections near water bodies, and some undulating forested areas. This mix provides a range of surfaces suitable for gravel bikes, from smoother sections to more challenging, unpaved tracks.

Best gravel bike trails around Pleasantville

  • The most popular gravel bike trail is Old Erie Rail…

Last updated: July 9, 2026

5.0

(1)

15

riders

#1.

Cross River reservoir dam – Cross River Reservoir loop from Fox Lane High School

43.6km

03:00

570m

570m

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

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Hard

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

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

Moderate

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

Hard

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

Hard

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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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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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The Bedford Oak is one of those rare living landmarks that quietly connects the past to the present. Estimated to be over 500 years old, this massive white oak has stood through centuries of change in Bedford, from Native American times to the Revolutionary War and beyond. Locals have always held it in high regard, and when development threatened its space in the 1970s, the community stepped up to save it. Thanks to their efforts, the tree and the land around it are now protected and cared for.

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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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The path is also easy to navigate in the summer heat, as it is nice and shady and often close to cooling water.

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Nice view of the Tarrytown Reservoir. The trail runs very close to the water, so you have a wonderful, unobstructed view across the reservoir. The path is popular with cyclists, so make sure you move to the edge if you want to stop to enjoy the great vistas.

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February 26, 2024, Cross River Bridge

As you pass over Cross River Bridge, you get a great view of the water below. The traffic is normally light, so you should be able to go slowly to enjoy the view. There is no shoulder on the road as it crosses the river, so it is not safe to stop while on the bridge.

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Frequently Asked Questions

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

The gravel biking landscape around Pleasantville is diverse, featuring former rail trails, scenic greenways, and routes that circle significant reservoirs and dams. You'll encounter a mix of surfaces, including paths along historic railway lines, both paved and unpaved sections near water bodies, and some undulating forested areas. This variety provides a range of experiences, from smoother gravel to more challenging, unpaved tracks.

Are there any easy or beginner-friendly gravel bike trails in Pleasantville?

While many routes in the area are rated moderate to difficult, the region's former rail trails offer some of the most consistent and relatively flat gravel surfaces. For a moderate experience that follows a historic rail line, consider the Old Erie Rail Trail (gravel) – Piermont Railway Station (historic) loop from Tarrytown. It's a good introduction to the area's gravel biking.

Which gravel bike routes are suitable for families in Pleasantville?

For families, routes that incorporate greenway sections and offer scenic views without extreme elevation changes are often preferred. The Van Cortlandt Greenway – Tarrytown Reservoir loop from Tarrytown combines greenway riding with views of the Tarrytown Reservoir, offering a pleasant moderate ride. Always check the route details for specific elevation and surface information to ensure it suits your family's abilities.

Are there any advanced or challenging gravel bike routes in Pleasantville?

Yes, Pleasantville offers several routes with more significant elevation gains and varied terrain for experienced gravel bikers. For a challenging ride with substantial climbing, consider the Cross River reservoir dam – Sutton Clock Tower loop from Village/Town of Mount Kisco, which features nearly 600 meters of elevation gain. Another demanding option is the Mianus River Gorge – Cross River Reservoir loop from Fox Lane High School.

What is the best season for gravel biking around Pleasantville?

Pleasantville's gravel trails are enjoyable across multiple seasons. Spring and fall offer pleasant temperatures and beautiful foliage, making them ideal. Summer can be great, especially on shaded sections, but be mindful of heat. Winter riding is possible, but conditions can vary with snow and ice, particularly on unpaved sections. Always check local weather and trail conditions before heading out.

Are there any gravel bike routes that are loop trails?

Yes, many of the popular gravel bike routes in Pleasantville 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 Tarrytown, the Van Cortlandt Greenway – Tarrytown Reservoir loop from Tarrytown, and the New Croton Dam – New Croton Dam loop from Ossining.

What are some scenic viewpoints or attractions along the gravel bike trails?

The region is rich with scenic spots, particularly around its many reservoirs and historic trails. You can enjoy views of the Tarrytown Reservoir and Kensico Reservoir, as well as the impressive New Croton Dam. Historic rail trails like the South County Trailway and North County Trailway also offer picturesque stretches.

Are there any dog-friendly gravel trails in Pleasantville?

Many multi-use trails in the Pleasantville area, including sections of the rail trails and greenways, are generally dog-friendly, provided dogs are kept on a leash. However, specific regulations can vary by park or trail section. It's always best to check the local rules for the particular trail you plan to ride to ensure it accommodates your furry companion.

What do other gravel bikers enjoy most about gravel biking in Pleasantville?

The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the diverse landscape, which offers a great mix of historic rail trails, scenic greenways, and routes around reservoirs. The variety of surfaces and the options for both moderate and more challenging rides are frequently highlighted.

Are there any long-distance gravel biking options in Pleasantville?

While individual routes typically range from 20 to 30 miles, the interconnected nature of the rail trails and greenways allows for longer rides by combining sections. For example, the Van Cortlandt Greenway – Tarrytown Reservoir loop from Tarrytown is one of the longer single routes at 27 miles, but you can extend your adventure by exploring connecting segments of the South County Trailway or North County Trailway.

Is public transport available to access gravel bike trails in Pleasantville?

Pleasantville and surrounding towns are served by Metro-North Railroad, which allows bikes on trains during off-peak hours. This can be a convenient way to access trailheads, especially for routes starting near train stations in towns like Tarrytown or Ossining. Always check Metro-North's bike policy and schedules before planning your trip.

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