4.8
(28)
377
riders
29
rides
Touring cycling routes around Chappaqua offer diverse landscapes, from extensive paved trail networks to roads with varied topography. The region features hardwood forests, scenic reservoirs like the Croton Reservoir, and natural stone outcroppings. Cyclists can find routes ranging from mostly flat, shaded paths to challenging climbs with significant elevation gains. This area provides a mix of serene natural beauty and varied terrain for touring cyclists.
Last updated: May 16, 2026
5.0
(4)
58
riders
50.3km
02:59
370m
370m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
37
riders
27.9km
01:36
120m
120m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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4.7
(3)
39
riders
37.0km
02:12
190m
190m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
32
riders
11.3km
01:02
170m
170m
Hard bike ride. Good fitness required. You may need to push your bike for some segments of this route.
5.0
(3)
16
riders
58.4km
04:03
530m
530m
Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route.
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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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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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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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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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There are over 25 touring cycling routes around Chappaqua, offering diverse experiences for cyclists. These routes are highly rated by the komoot community, with an average score of 4.9 stars.
Chappaqua offers a mix of terrain. You'll find extensive paved trail networks, such as the North County Trailway, which provides mostly flat and shaded paths ideal for leisurely rides. Additionally, there are roads with varied topography, including routes with significant elevation gains and challenging climbs like McKesson Hill and Roaring Brook, catering to more strenuous journeys.
Yes, Chappaqua is home to several family-friendly options. The North County Trailway, a 22-mile paved path, is particularly suitable for leisurely rides and family outings due to its flat, shaded nature. Routes like the Forest Peaceful Trail loop from Village of Briarcliff Manor are also easy and offer a relaxed experience through forested areas.
The routes around Chappaqua offer beautiful natural scenery. You can cycle through hardwood forests, past natural stone outcroppings, and alongside flowing brooks and streams. Many routes provide views of reservoirs, including the scenic Croton Reservoir, which you can cross via an old railroad bridge on the North County Trailway. You might also encounter blooming irises and daylilies at places like Rocky Hills on Old Roaring Brook Road.
Yes, many touring cycling routes in Chappaqua are designed as loops. For example, the Old Croton Dam Road Bridge – North County Trailway loop from Hawthorne is a popular moderate route that takes you past the Croton Reservoir. Another option is the Van Cortlandt Greenway – Woodlands Lake loop from Hawthorne, which leads through greenways and past Woodlands Lake.
Along the routes, you can encounter several interesting landmarks and natural attractions. The Red Bridge over the Croton Reservoir is a significant feature. You might also pass by the Kensico Reservoir or the Tarrytown Reservoir. For a unique natural sight, consider routes that pass near Pocantico Falls.
The best time for touring cycling in Chappaqua is generally during the spring, summer, and fall months. Spring offers blooming flora, while summer provides lush green landscapes and shaded trails. Autumn is particularly scenic with vibrant fall foliage. Always check local weather conditions before heading out, as varied terrain can be affected by rain or snow.
Absolutely. Chappaqua's touring cycling routes cater to all skill levels. You'll find easy, mostly flat rides on paved trails, such as the North County Trailway. For those seeking a challenge, there are moderate routes like the North County Trailway – The Pine Bridge Monument loop from Village of Briarcliff Manor, and more difficult routes with significant elevation gains on varied road terrain.
Parking is available at various access points to the trail networks. Gedney Park is an easy entry point to the North County Trailway and offers parking. Many trailheads and local parks provide designated parking areas for cyclists. It's advisable to check specific route starting points for detailed parking information.
Yes, the area is cycling-friendly and offers amenities. The Trailside Café in Yorktown is specifically mentioned as catering to trail users, providing a convenient stop for refreshments. You'll find other local establishments in towns and villages along the routes where you can pause for a break.
The komoot community highly rates touring cycling in Chappaqua, with an average score of 4.9 stars from over 20 reviews. Cyclists often praise the diverse landscapes, from peaceful forested trails to scenic reservoir views, and the well-maintained trail networks that offer options for all abilities. The variety of terrain, from flat paved paths to challenging climbs, is also a frequently highlighted aspect.
Chappaqua is accessible by public transport, particularly via the Metro-North Railroad's Harlem Line, which has a station in Chappaqua. This allows cyclists to bring their bikes and access routes directly from the town, or connect to the extensive trail networks like the North County Trailway.
Yes, several routes incorporate views of the Croton Reservoir. The Old Croton Dam Road Bridge – North County Trailway loop from Hawthorne specifically includes a section of the North County Trailway that crosses the scenic Croton Reservoir via an old railroad bridge, offering excellent views.


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