The best road cycling routes around Chappaqua
4.8
(25)
1,067
riders
21
rides
Road cycling routes around Chappaqua feature a diverse landscape of rolling hills and wooded terrain, providing both challenging climbs and relaxed, paved sections. The region is characterized by scenic reservoirs like Kensico and Croton, which offer picturesque views along many routes. Cyclists can also find extensive paved trailways, such as the North County Trailway, built on former railroad lines. This combination of natural features and infrastructure supports a range of road cycling experiences.
Best road cycling routes around Chappaqua
- The most popular road cycling route is Putnam Trail loop from Chappaqua, a 93.1 miles (149.8 km) trail that takes 6 hours 17 minutes to complete. This route is known for its significant elevation gain and challenging terrain.
- Another top favourite among local road cyclists is Van Cortlandt Greenway β Woodlands Lake loop from Chappaqua, an easy 28.3 miles (45.6 km) path. This shorter route offers a more relaxed ride through varied scenery.
- Local road cyclists also love the Maybrook Trailway β Quiet resting spot loop from Chappaqua, a 65.6 miles (105.5 km) trail leading through diverse landscapes, often completed in about 4 hours 34 minutes.
- Road cycling around Chappaqua is defined by rolling hills, wooded areas, and scenic reservoirs, with extensive paved trailways like the North County Trailway. The network offers options for different ability levels, from easy rides to more difficult climbs.
- The routes in Chappaqua are highly rated by the komoot community with an average score of 4.7 stars from more than 10 reviews. More than 800 road cyclists have used komoot to explore Chappaqua's varied terrain.
Last updated: June 26, 2026
5.0
(2)
23
riders
40.8km
01:57
320m
320m
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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3.0
(1)
17
riders
29.5km
01:18
240m
240m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
15
riders
25.5km
01:08
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
6
riders
82.5km
03:45
770m
770m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Tips from the Community
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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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 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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As you cross over an old rail trestle bridge, you are treated to great views of the New Croton Reservoir. The bridge is not open for car traffic, so you can stop on the path for a quick break to take in the views.
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Interesting tunnel under Kitchawan Road. The tunnel was constructed when this trail was still a railroad, but it has been adapted for hikers and cyclists. It is a fairly short tunnel, so you are able to walk through it without a light.
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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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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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Frequently Asked Questions
How many road cycling routes are available around Chappaqua?
There are over 20 road cycling routes around Chappaqua, catering to various skill levels. You'll find a mix of easy, moderate, and difficult options to explore the region's diverse landscapes.
What kind of terrain and elevation can I expect on Chappaqua's road cycling routes?
Chappaqua is characterized by its picturesque rolling hills and wooded terrain, offering both challenging climbs and enjoyable descents. Routes can feature significant elevation gains, such as the long slog up Seven Bridges from Route 100 or the many false summits on Hardscrabble. You'll also find ascents on McKesson Hill and Roaring Brook, alongside fast descents on Whippoorwill.
Are there easy or family-friendly road cycling routes in Chappaqua?
Yes, Chappaqua offers easier options suitable for recreational riders and families. The North County Trailway is a premier paved multi-use trail, mostly flat and shaded, ideal for a relaxed ride. An example of an easy loop is the Van Cortlandt Greenway β Woodlands Lake loop from Chappaqua, which is 45.6 km long.
Are there challenging routes for advanced road cyclists?
Absolutely. For experienced cyclists seeking a rigorous workout, Chappaqua provides routes with significant elevation gain and challenging terrain. The Putnam Trail loop from Chappaqua is a demanding 149.8 km route with over 1000 meters of elevation gain. Another difficult option is the Maybrook Trailway β Quiet resting spot loop from Chappaqua, which is 105.5 km long.
What scenic features or landmarks can I see along the road cycling routes?
Many routes offer stunning views of the region's reservoirs, such as the beautiful Kensico Reservoir and the Tarrytown Reservoir. The Croton Reservoir features a scenic crossing on an old railroad bridge as part of the North County Trailway. You might also encounter historic stone walls lining some roadways, adding to the area's charm, and even the Pocantico Falls.
Where are good places to park or access the road cycling trails?
A popular starting point for rides on the North County Trailway is the Millwood area, where the trail crosses Route 120. Gedney Park also provides an easy entry point to the North County Trailway. For specific routes, check the individual tour details on komoot for recommended starting points and parking information.
Can I reach the cycling routes by public transport?
Chappaqua is served by Metro-North Railroad, making it accessible by public transport from New York City. From the Chappaqua station, you can connect to various local roads and begin your cycling adventure. The North County Trailway is also accessible at several points along its length, some of which may be near public transport stops.
What is the best time of year for road biking in Chappaqua?
The spring, summer, and fall months generally offer the best conditions for road biking in Chappaqua. Spring brings blooming landscapes, while fall showcases vibrant foliage. Summers are warm, but the wooded sections of trails like the North County Trailway can offer shade. Always check local weather forecasts before heading out.
What do other road cyclists enjoy most about road cycling in Chappaqua?
The road cycling routes around Chappaqua are highly rated by the komoot community, with an average score of 4.8 stars from more than 10 reviews. Cyclists often praise the diverse landscape, which offers a good mix of challenging hills and scenic, relaxed paved sections, as well as the beautiful reservoir views.
Are there any long-distance road cycling routes near Chappaqua?
Yes, the North County Trailway connects to the 12-mile Putnam Trailway to the north and the 23-mile South County Trailway to the south, creating an extensive network for longer rides. This allows for continuous cycling over significant distances, offering a comprehensive exploration of the region.
Are there any specific loop routes recommended for road cycling?
Chappaqua offers several excellent loop routes. Beyond the popular Putnam Trail loop from Chappaqua, you can also explore the Downtown Piermont β Tarrytown Lakes loop from Chappaqua, a moderate 60.1 km ride that takes you past the scenic Tarrytown Lakes area.
Are there any official maps or brochures for the trailways in the area?
Yes, for detailed information on the North County Trailway and other trailways in Westchester County, you can consult official resources. A map and brochure for the Westchester County Trailways can be found on the county's parks website: Westchester County Trailways Brochure Map.
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