4.5
(40)
1,191
riders
93
rides
Road cycling around Pleasantville, NY, offers diverse terrain across forested hills, valleys, and along waterways. The region features a network of crushed stone carriage roads and paved trails, including sections of the North County Trailway and the Old Croton Aqueduct State Historic Trail. Riders can expect routes that traverse varied landscapes, from open fields to tree-lined streets. The area's topography includes gentle gradients and some more challenging ascents, providing a range of experiences for road cyclists.
Last updated: August 6, 2026
5.0
(1)
89
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
18
riders
87.5km
03:55
830m
830m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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11
riders
87.1km
04:20
960m
960m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
10
riders
14.7km
00:35
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
6
riders
25.6km
01:14
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Great trail and only occasional crossing traffic
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Cobamong Pond is a serene small body of water nestled in the heart of Armonk. It's a great place to take a break to enjoy a quiet escape from the city's hustle and bustle during your ride.
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Great stretch of a well paved and quiet road. There is little to no shoulder though, so that might put off les experienced riders.
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Nice view of Kensico Reservoir from the bridge over Kensico Dam. The reservoir was created in 1885 when the Bronx and Byram rivers were dammed. The water in the reservoir is used as drinking water for New York City.
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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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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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There are over 90 road cycling routes around Pleasantville, offering a wide variety of experiences. These include 16 easy routes, 61 moderate routes, and 18 difficult routes, catering to all skill levels.
Road cycling in Pleasantville features diverse terrain, including forested hills, valleys, and pathways along waterways. You'll find a mix of crushed stone carriage roads and paved trails, such as sections of the North County Trailway and the Old Croton Aqueduct State Historic Trail. Routes traverse open fields, tree-lined streets, and offer both gentle gradients and some more challenging ascents.
Yes, Pleasantville offers several easy road cycling routes perfect for beginners or families. These routes often feature paved surfaces and gentler gradients. An example is Van Cortlandt Greenway – Woodlands Lake loop from Chappaqua, which is an easy 28.3-mile (45.6 km) trail.
Absolutely. For experienced cyclists seeking a challenge, Pleasantville has several difficult routes. The Putnam Trail loop from Chappaqua is a notable example, covering 93.1 miles (149.8 km) with significant elevation changes, offering an extensive and demanding ride.
Many routes offer scenic views of the Hudson River, especially along sections like the Old Croton Aqueduct State Historic Trail. You can also cycle past beautiful natural features such as Swan Lake and the Pocantico River within the Rockefeller State Park Preserve. The Kensico Reservoir and Tarrytown Reservoir are also prominent features you might encounter.
Yes, the region is rich in history. The Old Croton Aqueduct State Historic Trail itself is a historical landmark, offering insights into 19th-century engineering. You might also pass by the Red Bridge over the Croton Reservoir, a notable structure in the area.
Route lengths vary significantly, from shorter loops to extensive long-distance rides. For instance, an easy route like The Pine Bridge Monument – North County Trailway loop from Pleasantville is about 24.7 miles (39.7 km) and takes around 1 hour 41 minutes. More challenging routes, such as the Maybrook Trailway – Quiet resting spot loop from Chappaqua, can be over 65 miles (105 km) and take several hours to complete.
Yes, many road cycling routes in Pleasantville are designed as loops, allowing you to start and end at the same point. Examples include The Pine Bridge Monument – North County Trailway loop from Pleasantville and the Downtown Piermont – Tarrytown Lakes loop from Chappaqua.
The area is highly rated by the komoot community, with an average score of 4.7 stars from over 30 reviews. Reviewers often praise the diverse terrain, from forested hills to river pathways, and the well-maintained trails that cater to various ability levels. The scenic beauty and the network of interconnected trails are frequently highlighted.
Yes, the South County Trailway is particularly noted as a primary cycling route with asphalted segments, making it ideal for road bikes. Sections of the North County Trailway also offer paved surfaces, providing smooth riding experiences.
Absolutely. Several routes will take you past significant bodies of water. You can explore areas around the Kensico Reservoir and the Tarrytown Reservoir, offering picturesque views and tranquil settings for your ride.
Yes, Pleasantville has a local bike shop called 'Ride of Pleasantville,' indicating a supportive community for cyclists. This can be a convenient resource for any last-minute supplies or repairs you might need.


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