4.6
(37)
2,552
riders
105
rides
Road cycling routes around Chestnut Ridge feature a diverse landscape with varied terrain, offering options for different fitness levels. The region is characterized by mostly well-paved surfaces, forested areas, and wooded ravines, providing smooth riding conditions. Cyclists can expect routes with significant elevation changes, ranging from moderate climbs to more challenging ascents. This area presents a compelling destination for road cyclists seeking both scenic beauty and physical challenge.
Last updated: June 27, 2026
4.5
(4)
732
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
66
riders
189km
09:17
1,970m
1,970m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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21
riders
58.1km
02:42
660m
660m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
32
riders
44.2km
01:51
310m
310m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
59.4km
03:08
840m
840m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Chestnut Ridge
This is a nice uphill challenge. Just shift to a low gear. You can do it.
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Beautiful route, narrow road with car traffic
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This road is a treat whether you're heading up or downhill. Lake Sebago is gorgeous as well and a great place to have a water break after the climb.
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Originally a small pond, Lake Welch was increased to its current size when a dam was built in 1942. It boasts the largest beach in Harriman State Park as well as multiple picnic and bbq areas.
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Little Long Pond is beautiful any time of year, but if you happen to be riding along Kanawauke Road during the fall color season you'll be in for a real treat!
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There are over 120 road cycling routes around Chestnut Ridge, catering to various skill levels. You'll find a good mix, with about 35 easy routes, 70 moderate routes, and 18 more challenging options.
Road cycling routes in Chestnut Ridge feature a diverse landscape. You can expect mostly well-paved surfaces, offering smooth riding conditions through forested areas and wooded ravines. Many routes include significant elevation changes, from moderate climbs to more demanding ascents, providing both scenic beauty and physical challenge.
Yes, Chestnut Ridge offers several challenging routes. For instance, the Hudson River Greenway – The Little Red Lighthouse loop from Nanuet is a difficult 82.3-mile route with over 1,000 meters of elevation gain. Another demanding option is the Bear Mountain Climb – View from Bear Mountain Summit loop from Nanuet, which covers 57 miles with a substantial climb to Bear Mountain Summit.
For those seeking an easier ride, Chestnut Ridge still offers enjoyable options. The Ridgewood – Wild Duck Pond loop from Monsey is an easy 24.5-mile route with manageable elevation, perfect for a more relaxed cycling experience.
While cycling, you'll encounter beautiful forests and wooded ravines. The broader Chestnut Ridge area is known for unique natural attractions like the Eternal Flame Falls in Chestnut Ridge Park (Erie County, NY), where a natural flame burns at the base of a waterfall. You might also pass by the Ramapo River or Pine Meadow Lake, offering scenic views.
Yes, you can explore dedicated cycling paths. The New York State Bike Route 9 – Tappan Zee Bridge Section offers a notable cycling experience. Additionally, parts of the Hudson River Greenway are featured in routes, providing extensive riding along the river.
The road cycling routes in Chestnut Ridge are highly rated by the komoot community, with an average score of 4.5 stars from over 20 reviews. Cyclists often praise the varied terrain, well-paved surfaces, and the scenic forested landscapes that make for an engaging ride.
Yes, depending on your chosen route, you may find options for refreshments. For example, the Boxer Donut & Espresso Bar is a highlight that could serve as a convenient stop for cyclists.
Chestnut Ridge offers enjoyable road cycling through much of the year. The diverse terrain and forested areas are particularly beautiful in spring and autumn when the foliage changes. Summer provides warm weather, while late spring and early fall often offer ideal temperatures for longer rides.
For those looking for longer rides, Chestnut Ridge has options that extend over significant distances. The S-Curve Hill beneath the George Washington Bridge – Hudson River Greenway loop from Pearl River is a challenging route spanning over 130 miles (210 km) with substantial elevation gain, perfect for an all-day adventure.
Absolutely. Many routes in Chestnut Ridge combine moderate climbs with rewarding scenic views. The Climb up to Alpine – 9W Market loop from Pearl River is a moderate 42.4-mile path that includes a significant climb to Alpine, providing varied terrain and beautiful vistas along the way.


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