5.0
(2)
25
riders
4
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.
Last updated: May 28, 2026
5.0
(1)
14
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
2
riders
43.5km
02:35
290m
290m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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9
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
7
riders
37.6km
02:39
600m
600m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
47.1km
02:54
300m
300m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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Piermont is a quaint, small town along the Hudson River. There are several restaurants, cafés, and shops in the town, so it is a good place for a break if you are hiking the Long Path.
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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 section of the New York State Bike Route is a popular stretch, especially around the Tappan Zee Bridge. It attracts many cyclists on weekends.
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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