4.6
(35)
999
riders
82
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: September 2, 2026
5.0
(2)
29
riders
45.2km
02:10
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
18
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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15
riders
25.4km
01:08
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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.
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A perfect mid-ride stop with great donuts and coffee, but also a bike rack out back and a water bottle filling station outside. Get here early to beat the crowds on a weekend.
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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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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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The North County Trailway is a 20-mile rail trail from Baldwin Place to Sleepy Hollow. The section around Millwood passes several Revolutionary War monuments, and goes through Echo Lake State Park. The trail is slightly downhill if you are going north to south.
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You can't ride bikes on the trails, but a nice spot for lunch (byo) when rambling in the CT/NY liminal zone. Lock your bike (or drive there) for a short but sweet hike.
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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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Brown Preserve is a beautiful, protected woodland that Stanwich Road runs through. It is a great section of shady road to ride through, especially on a hot summer's day.
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You'll find a gap in the trees here, giving excellent wide views of the cove. It looks particularly good during the autumn, when the trees turn a golden, amber and crimson colour.
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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 β 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 β 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 β 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 β North County Trailway loop from Pleasantville and the Downtown Piermont β 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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