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Road cycling routes
United States
New York
Westchester County

Shrub Oak

The best road cycling routes around Shrub Oak

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.

Best road cycling routes around Shrub Oak

  • The most…

Last updated: August 8, 2026

5.0

(1)

67

riders

#1.

View from bridge – The Pine Bridge Monument loop from Shenorock

41.7km

01:48

370m

370m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Tips from the Community

Lisa
June 23, 2025, Trailside Café

A great place to stop for a snack and a quick drink.

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amazingly tough but fast climb with a 14% avg

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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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Frequently Asked Questions

How many road cycling routes are available around Shrub Oak?

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.

What kind of terrain can I expect on road cycling routes in Shrub Oak?

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.

Are there road cycling routes suitable for beginners or families in Shrub Oak?

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.

Are there challenging road cycling routes for experienced cyclists in Shrub Oak?

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.

What are some scenic highlights or landmarks I can see while road cycling in Shrub Oak?

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.

Are there any loop routes for road cycling in the area?

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.

What do other cyclists say about road cycling in Shrub Oak?

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.

What is the best time of year for road cycling in Shrub Oak?

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.

Are there any routes that offer views of the Croton Reservoir system?

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.

Can I find routes that pass by historical sites?

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.

Are there any cafes or resting spots along the routes?

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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