5.0
(2)
51
riders
6
rides
Gravel biking around Chappaqua offers diverse terrain across Westchester County, characterized by its hilly landscape and extensive trail networks. The region provides a mix of dirt and paved surfaces, allowing for varied routes that minimize traffic exposure. Cyclists can explore areas with lush greenery, woodlands, and open fields, making it suitable for mixed-surface cycling. This environment supports a range of gravel biking experiences, from challenging climbs to scenic, winding paths around numerous reservoirs.
Last updated: June 28, 2026
5.0
(1)
15
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
riders
Hard gravel ride. Good fitness required. You may need to push your bike for some segments of this route.

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9
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
9
riders
37.6km
02:39
600m
600m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
39.0km
02:39
540m
540m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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 massive reservoir is about nine miles long, stretching through five different towns. There's a gorgeous, cascading spillway on the west of the reservoir. In this particular spot, you can access the shore of the reservoir just off Croton Lake Road, or via the Teatown-Kitchawan Trail.
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Croton Point Park is a popular park on Croton Bay. The park has a lot to offer, including hiking trails, a pavilion, a playground, and a beach.
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Already climbing from Brookfarm Rd East. Gravel sector maxes at about 10%. Careful on the decent on the other side...
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This is a wonderful, quiet stretch of road. It winds through woodlands, and you will occasionally pass some beautiful houses.
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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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This lovely smooth, paved road goes through Ward Pound Ridge Reservation over rolling hills. This is an especially pretty road to ride in the fall as the leaves change from green to orange, yellow, and red.
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Gravel biking around Chappaqua offers a diverse mix of terrain. You'll encounter hilly landscapes, extensive trail networks, and a blend of dirt and paved surfaces. The region is characterized by lush greenery, woodlands, and open fields, providing varied routes that minimize traffic exposure and offer a true mixed-surface cycling experience.
Yes, many of the gravel routes around Chappaqua feature significant elevation changes and are rated as difficult. For example, the Mianus River Gorge – Cross River Reservoir loop from Fox Lane High School includes over 640 meters of ascent, providing a substantial challenge for experienced riders. The area's hilly nature ensures plenty of opportunities for demanding climbs.
The Chappaqua area is rich in natural beauty and notable landmarks. You can expect to see prominent reservoirs like the Kensico Reservoir and Tarrytown Reservoir, offering scenic waterside views. Other highlights include the impressive Pocantico Falls and the historic Red Bridge over the Croton Reservoir. Many routes also pass through extensive park preserves with woodlands and meadows.
While many routes in Chappaqua are rated as difficult, some sections of the broader trail networks, like the Old Croton Aqueduct State Historic Trail or the South County Trail, may offer flatter, more accessible paths suitable for families. Rockefeller State Park Preserve also features crushed stone carriage roads that are generally less technical, though specific gravel bike routes designed for families might require careful selection based on individual fitness levels.
Yes, parking is generally available near trailheads and access points for many of the gravel routes. For example, the Old Croton Dam Road Bridge – New Croton Dam loop starts from Donald J. Trump State Park – French Hill Section, which typically has parking facilities. It's advisable to check specific starting points for parking availability before your ride.
The spring and fall seasons are generally ideal for gravel biking in Chappaqua. The weather is typically mild, and the natural landscapes are particularly vibrant with blooming foliage in spring or colorful leaves in autumn. Summer can also be pleasant, though it can get warm, while winter riding might be possible depending on snow and ice conditions, especially on unpaved sections.
Yes, many of the popular gravel bike routes in Chappaqua are designed as loops, allowing you to start and end at the same point. Examples include the Cross River reservoir dam – Sutton Clock Tower loop and the New Croton Dam – New Croton Dam loop. These circular routes offer convenience and a varied riding experience without retracing your path.
The gravel biking routes around Chappaqua are highly rated by the komoot community, with an average score of 5.0 stars. Users frequently praise the diverse terrain, the scenic views of reservoirs and natural preserves, and the engaging mix of dirt and paved surfaces that make for a rewarding mixed-surface cycling experience.
Chappaqua is served by Metro-North Railroad, making it accessible by public transport from New York City. While some trailheads might be within cycling distance from the train station, direct public transport access to all starting points can vary. It's recommended to check local bus routes or plan a short ride from the station to your desired trail access.
While many of the featured routes are rated as difficult, the region does offer sections that are more suitable for beginners. Areas like Rockefeller State Park Preserve have extensive crushed stone carriage roads that provide a smoother, less technical surface. For a more moderate option, the New Croton Dam – New Croton Dam loop from Ossining is rated as moderate and offers a good balance for those looking for a less intense ride.
Many parks and preserves in the Chappaqua area, such as Rockefeller State Park Preserve and Gedney Park, are dog-friendly, often requiring dogs to be on a leash. However, specific regulations can vary by trail and land management authority. It's always best to check the rules for the particular trail or park you plan to visit to ensure dogs are permitted on the cycling paths.
Chappaqua and nearby towns like Mount Kisco and Ossining offer various cafes, restaurants, and shops where you can refuel before or after your ride. While not directly on every trail, these towns are typically within a short distance of many starting points and provide convenient options for food and drink.


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