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Routes
Road cycling routes
United States
New York
Westchester County

Sleepy Hollow

The best road cycling routes around Sleepy Hollow

4.4

(66)

2,395

riders

78

rides

Road cycling around Sleepy Hollow, New York, offers a diverse landscape characterized by rolling hills, lush forests, and scenic views of the Hudson River. The region's topography provides varied terrain, from gentle stretches along historic paths to more challenging climbs. This area is well-suited for road cyclists seeking routes that combine natural beauty with a mix of elevation changes. The extensive network of routes caters to various fitness levels.

Best road cycling routes around Sleepy Hollow

  • The most popular road…

Last updated: April 28, 2026

29

riders

#1.

New Croton Reservoir Loop

64.2km

03:14

640m

630m

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

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Moderate

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

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

Moderate

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Tips from the Community

mtm05005
July 8, 2025, Downtown Piermont

Piermont is a quaint, small town along the Hudson River. There are several restaurants, cafés, and shops in the town, so it is a good place for a break if you are hiking the Long Path.

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Once a reservoir for drinking water, this was officially decommissioned in 1993 — leaving it as a lake held back by a dam. The resulting park has quickly become a recreation gem in Tarrytown, with hiking and biking trails, pretty lookout points, and opportunities for kayaking and fishing.

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Wonderful gravel path along the Hudson

Translated by Google

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Lisa
September 26, 2024, Rockland Lake South

This 256-acre lake might seem pretty shrimpy alongside the mighty Hudson River to the east, but the lake has a nice road-ride loop all the way around it, and a small jetty leading into the water.

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This section of the New York State Bike Route is a popular stretch, especially around the Tappan Zee Bridge. It attracts many cyclists on weekends.

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Very popular stretch here that leads to and from the Tappan Zee. Gets lots of cyclists on weekends when the weather is good.

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This route gets busy, obviously, so hit it early when the weather's good.

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At Painters Point, perched 102 feet high on the Mario M. Cuomo Zee Bridge, find inspiration in the majestic Hudson River scenery. A unique bronze and wood structure frames views of the river and Hook Mountain, inviting reflection and appreciation. Join the long legacy of artists moved by the Hudson's beauty as you stand on this elevated viewpoint.

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Frequently Asked Questions

How many road cycling routes are available around Sleepy Hollow?

There are over 85 road cycling routes around Sleepy Hollow, offering a diverse range of experiences. These include 30 easy routes, 45 moderate routes, and 10 more challenging options for experienced cyclists.

What kind of terrain can I expect on road cycling routes in Sleepy Hollow?

Road cycling around Sleepy Hollow is characterized by rolling hills, lush forests, and scenic views of the Hudson River. You'll find a mix of gentle stretches and more challenging climbs, catering to various fitness levels. The region's topography ensures a varied and engaging ride.

Are there road cycling routes suitable for beginners in Sleepy Hollow?

Yes, Sleepy Hollow offers 30 easy road cycling routes. These routes typically feature less elevation gain and shorter distances, making them ideal for beginners or those looking for a more relaxed ride.

What do other cyclists say about road cycling in Sleepy Hollow?

The road cycling routes in Sleepy Hollow are highly rated by the komoot community, with an average score of 4.6 stars from over 70 reviews. Cyclists often praise the varied terrain, beautiful Hudson River views, and the well-maintained paths.

Are there any loop road cycling routes around Sleepy Hollow?

Yes, many routes in the area are loops. For example, the New Croton Reservoir Loop is a popular moderate route that takes you around the reservoir. Another option is The Pine Bridge Monument – Quiet resting spot loop from Tarrytown, which offers a longer, scenic ride.

What natural features or landmarks can I see while road cycling in Sleepy Hollow?

Many routes offer picturesque views of the Hudson River. You can also encounter reservoirs like the Kensico Reservoir and Tarrytown Reservoir. The historic Old Croton Aqueduct Trail is also a significant feature in the area, popular for cycling.

Are there any specific points of interest along the road cycling routes?

Yes, you can find various points of interest. The South County Trailway and Hudson River Waterfront Trail at Nyack Beach State Park are notable cycling paths. For a quick stop, the 9W Market is a popular spot for cyclists.

Are there any family-friendly road cycling routes in Sleepy Hollow?

While specific 'family-friendly' road cycling routes aren't explicitly categorized, the 30 easy routes available are generally suitable for families looking for less strenuous rides. The Old Croton Aqueduct Trail, with its relatively flat and historic path, is also a good option for a family outing.

Where can I find scenic viewpoints along the road cycling routes?

Many routes offer stunning views of the Hudson River. The Rockwood Hall section of Rockefeller State Park Preserve provides panoramic vistas. Routes that pass by the New Croton Reservoir, such as the New Croton Reservoir Loop, also offer beautiful scenery.

What are some longer road cycling routes for experienced riders?

For experienced riders seeking longer distances, routes like The Pine Bridge Monument – Quiet resting spot loop from Tarrytown, at 54.7 miles, or the 9W Market – Climb up to Alpine loop from Tarrytown, at 44.4 miles with notable climbs, provide a good challenge.

Are there any coffee shops or places to refuel near the road cycling routes?

Yes, the 9W Market is a well-known stop for cyclists. Additionally, towns like Tarrytown, which serve as starting points for several routes, offer various cafes and establishments where you can refuel.

Can I access the Old Croton Aqueduct Trail for road cycling?

The Old Croton Aqueduct Trail is a significant highlight in the region, popular for both walking and biking. While it's a multi-use path, its 26.2-mile length offers a unique experience for cyclists, providing stunning views of the Hudson River Valley.

What is the best time of year to go road cycling in Sleepy Hollow?

The spring and fall seasons generally offer the most pleasant conditions for road cycling in Sleepy Hollow, with mild temperatures and beautiful foliage. Summer can also be enjoyable, though it may be warmer. Winter cycling is possible but requires appropriate gear for colder temperatures and potential icy conditions.

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