4.8
(12)
556
riders
30
rides
Road cycling routes around Shrub Oak, located within Westchester County, traverse a landscape characterized by rolling hills and extensive forested terrain. The region features a network of paved surfaces, offering views of the Croton Reservoir system. Cyclists can expect routes with varied elevation gains through woodlands predominantly composed of oak and other deciduous trees. The area provides diverse terrain for road cyclists, including proximity to the Hudson River and large reservoirs.
Last updated: August 8, 2026
5.0
(1)
67
riders
41.7km
01:48
370m
370m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
62
riders
38.9km
01:48
440m
440m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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22
riders
67.6km
02:51
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
16
riders
62.8km
03:10
870m
870m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
14
riders
30.0km
01:24
300m
300m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Lots of benches just off the paved trail to rest your legs or to enjoy the scenery.
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The North County Trailway is a 20-mile rail trail from Baldwin Place to Sleepy Hollow. The section around Yorktown Heights is particularly scenic. It passes several Revolutionary War monuments and an old railway depot. The section ends at a beautiful old railway trestle bridge.
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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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There are over 25 road cycling routes around Shrub Oak, offering a variety of experiences for cyclists. The komoot community has explored these routes over 400 times, indicating their popularity.
Road cycling routes in Shrub Oak are characterized by rolling hills and extensive forested areas, primarily composed of oak and other deciduous trees. You'll find a network of paved surfaces, often providing shaded paths and scenic views of the Croton Reservoir system and the Hudson River.
While most routes in Shrub Oak are rated as moderate, the region offers options that can be enjoyable for those seeking a less strenuous ride. The North County Trailway, for instance, provides smooth sections and scenic views, making it suitable for moderate rides. However, there are no routes specifically classified as 'easy' in the immediate guide data.
Yes, Shrub Oak offers routes with significant elevation gains that can challenge experienced cyclists. For example, the route Perkins Memorial Tower – Bear Mountain Bridge loop from City of Peekskill features over 720 meters of elevation gain, providing a demanding ride. The overall landscape of rolling hills contributes to varied difficulty levels.
The area is rich with natural beauty and points of interest. You can cycle past the impressive New Croton Dam, enjoy views from the Red Bridge over the Croton Reservoir, or take in panoramic vistas from View from Turkey Mountain. Many routes also offer views of the expansive Croton Reservoir system.
Yes, many of the road cycling routes around Shrub Oak are designed as loops. Popular options include View from bridge – The Pine Bridge Monument loop from Shenorock and Lake Casse – Quiet resting spot loop from Shenorock, both offering circular paths to explore the region's beauty.
The road cycling routes in Shrub Oak are highly rated by the komoot community, with an average score of 4.8 stars from over 14 reviews. Cyclists often praise the scenic views, varied terrain, and the opportunity to explore the picturesque landscapes of Westchester County.
Given the extensive forested areas with deciduous trees, spring, summer, and fall are excellent times for road cycling in Shrub Oak. Spring brings fresh foliage, summer offers shaded routes, and autumn provides stunning fall colors, making for a picturesque ride. Winter cycling might be possible, but conditions would depend on snow and ice.
Absolutely. The Croton Reservoir system is a central feature of the region, and many road cycling routes offer breathtaking views. The New Croton Dam – Trailside Café loop from Parking at Valeria is one such route that provides excellent vistas of the reservoir and its impressive dam.
Yes, some routes incorporate historical elements. For instance, the View from bridge – The Pine Bridge Monument loop from Shenorock passes by The Pine Bridge Monument, offering a touch of local history amidst your ride. The North County Trailway also passes by historical markers, including a memorial to the Battle of Pines Bridge.
Some routes are named with potential resting spots in mind. For example, the New Croton Dam – Trailside Café loop from Parking at Valeria suggests a trailside café, and the Lake Casse – Quiet resting spot loop from Shenorock indicates a peaceful place to pause. These can be good points to plan a break during your ride.


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