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United States
New York
Westchester County

Pleasantville

The best cycling routes around Pleasantville

4.7

(40)

549

riders

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Touring cycling routes around Pleasantville feature diverse landscapes, including forested hills, river valleys, and open fields. The region is characterized by well-maintained trails such as the Old Croton Aqueduct State Historic Trail and the South County Trailway, offering scenic views and varied terrain. Rockefeller State Park Preserve provides extensive crushed stone carriage roads, while Graham Hills Park offers trails for mountain biking.

Best touring cycling routes around Pleasantville

  • The most popular touring cycling route is Old Croton Dam Road Bridge…

Last updated: June 28, 2026

5.0

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#1.

Old Croton Dam Road Bridge – North County Trailway loop from Hawthorne

50.3km

02:59

370m

370m

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

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Moderate

4.0

(3)

39

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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

Moderate

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

Moderate

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

Hard
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Popular around Pleasantville

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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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Ed Mal
August 10, 2025, Stewart's Farm

Coffee an Peach ride

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Lisa
June 23, 2025, Trailside Café

A great place to stop for a snack and a quick drink.

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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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Great section of the North County Trailway. The paved path passes through a beautiful wooded area. As the trail gets to Tarrytown Reservior, there is an area with benches for a break.

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Historic building which used to be the Eastview Pumping Station. It was built in 1897, and up until 1993, it was used to clean and move the vil­lage’s drinking water. The building is not open to visitors, but from some points on the trail, you can see into the old buildings.

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The North County Trailway is a 20-mile rail trail from Baldwin Place to Sleepy Hollow. The section around Yorktown Heights is particularly scenic. It passes several Revolutionary War monuments and an old railway depot. The section ends at a beautiful old railway trestle bridge.

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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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Frequently Asked Questions

How many touring cycling routes are available around Pleasantville?

There are over 40 touring cycling routes available around Pleasantville, offering a wide range of options for different skill levels and preferences. You'll find everything from easy loops to more challenging moderate routes.

What kind of terrain can I expect on touring cycling routes in Pleasantville?

Pleasantville's touring cycling routes feature diverse landscapes, including forested hills, river valleys, and open fields. Many trails, like those in Rockefeller State Park Preserve, utilize crushed stone carriage roads, while others, such as the South County Trailway, offer asphalted segments. You'll encounter varied terrain suitable for touring bikes.

Are there touring cycling routes suitable for beginners or families with children?

Yes, Pleasantville offers several easy touring cycling routes perfect for beginners and families. For a tranquil experience through wooded areas, consider the Forest Peaceful Trail loop from Village of Briarcliff Manor, which is an easy 16.3-mile path. The South County Trailway is also known for its well-maintained, family-friendly sections.

What are some longer or more challenging touring cycling routes in the area?

For those seeking a moderate challenge, the Old Croton Dam Road Bridge – North County Trailway loop from Hawthorne is a popular choice. This 31.2-mile route connects historical landmarks with scenic trailways and typically takes around 3 hours to complete. Another moderate option is the Van Cortlandt Greenway – Woodlands Lake loop from Hawthorne, a 23.0-mile trail through greenways.

What natural features or landmarks can I see along the touring cycling routes?

Pleasantville's routes offer access to several natural and historical landmarks. You can cycle along the scenic North County Trailway, enjoy views of the Hudson River from the Old Croton Aqueduct State Historic Trail, or pass by beautiful bodies of water like Kensico Reservoir and Tarrytown Reservoir. Rockefeller State Park Preserve also features Swan Lake and the Pocantico River.

Are there any circular touring cycling routes in Pleasantville?

Yes, many touring cycling routes in Pleasantville are designed as loops, offering convenient starting and ending points. Examples include the Old Croton Dam Road Bridge – North County Trailway loop from Hawthorne and the Forest Peaceful Trail loop from Village of Briarcliff Manor. These loops allow you to experience diverse scenery without retracing your steps.

What is the best time of year to go touring cycling in Pleasantville?

The spring, summer, and fall months generally offer the best conditions for touring cycling in Pleasantville, with pleasant temperatures and vibrant scenery. The Rockefeller State Park Preserve is particularly beautiful in autumn. While some trails may be accessible in winter for cross-country skiing or snowshoeing, cycling conditions can vary depending on snow and ice.

Are dogs allowed on the touring cycling trails in Pleasantville?

Many parks and trails in the Pleasantville area, such as the Rockefeller State Park Preserve, are dog-friendly, typically requiring dogs to be on a leash. It's always best to check specific regulations for each trail or park you plan to visit, as rules can vary.

Where can I find parking or access public transport for the cycling routes?

Parking is generally available at trailheads and designated parking areas for major parks like Rockefeller State Park Preserve and Graham Hills Park. For public transport, the South County Trailway is described as a gateway cycling route from New York City, suggesting accessibility from urban areas, though specific public transport links to trailheads should be checked locally.

What do other touring cyclists enjoy most about cycling in Pleasantville?

The touring cycling routes in Pleasantville are highly rated by the komoot community, with an average score of 4.9 stars from over 30 reviews. Cyclists often praise the well-maintained trails, the diverse landscapes ranging from forested areas to river valleys, and the historical significance of routes like the Old Croton Aqueduct State Historic Trail.

Are there any bike shops or services available in Pleasantville?

Yes, Pleasantville supports its cycling community with local resources. "Ride of Pleasantville" is a local bike shop that caters to various types of cyclists, providing bicycle repair services, tune-ups, and sales, ensuring you have support for your touring adventures.

Can I combine touring cycling with other outdoor activities in Pleasantville?

Absolutely. Many areas popular for touring cycling, such as Rockefeller State Park Preserve, also offer opportunities for hiking, jogging, and birdwatching. During winter, the preserve transforms for cross-country skiing and snowshoeing. Graham Hills Park, while known for mountain biking, also has scenic trails for other activities.

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