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Road cycling routes
United States
California
Marin County

Sleepy Hollow

The best road cycling routes around Sleepy Hollow

4.5

(178)

7,493

riders

98

rides

Road cycling around Sleepy Hollow, NY, features diverse landscapes with rolling hills, lush forests, and scenic views of the Hudson River. The region offers varied terrain, including gentle stretches and climbs with significant elevation gain. Cyclists can explore areas around reservoirs and historic linear state parks, providing a blend of natural beauty and dedicated infrastructure. The landscape is characterized by its picturesque backdrop for rides, catering to different fitness levels.

Best road cycling routes in Sleepy Hollow

  • The most popular…

Last updated: July 8, 2026

5.0

(7)

405

riders

#1.

Nicasio Reservoir loop from Marin Civic Center

80.2km

03:50

980m

980m

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

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Hard

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. Mostly well-paved surfaces and easy to ride.

Moderate

5.0

(3)

99

riders

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

Hard

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

Hard
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Tips from the Community

serge 🚶🐉😊🇧🇪
October 12, 2025, Marin Museum of Bicycling

An absolute must-see for cycling enthusiasts! This museum in Fairfax tells the story of nearly 200 years of cycling history, from 19th-century velocipedes to modern racing bikes. It's also home to the Mountain Bike Hall of Fame, featuring unique specimens and stories about the pioneers of mountain biking. The collection is impressive and authentic—no replicas, but real bicycles that showcase the evolution of technology and design. An inspiring place where you can truly feel the passion for cycling.

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Traveler
June 27, 2025, Seven Sisters

Paved section riding on the ridge between Pan Toll Road and Fairfax-Bolinas Road where it contains as Bolinas Ridge Trail, with spectacular views along the way toward the Pacific Ocean and Stinson Beach far below. The road is open during daylight hours only, in winter that means 9am to sunset.

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Lots of fun shops

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Andrus
May 26, 2025, Alpine Dam

Constructed in 1917 this dam forms Alpine Lake, which sites between Kent and Bon Tempe Lakes. The road across the top of the dam make it a great place to ride on a loop around the lake.

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Andrus
May 25, 2025, Alpine Lake

This lake was formed by the building of Alpine Dam in 1917. It sits between Kent Lake and Bon Tempe Lake, and is popular for a variety of outdoor activities.

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Set beneath the towering trees of Mount Tam, Rock Springs is the perfect jumping-off point for scenic hikes and quiet picnics—where trails, wildlife, and wide-open views begin.

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Get there early limited parking

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Love this trial to and from SFD

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Frequently Asked Questions

How many road cycling routes are available around Sleepy Hollow?

There are nearly 100 road cycling routes available around Sleepy Hollow, catering to various skill levels. This includes 28 easy routes, 41 moderate routes, and 26 difficult routes, ensuring options for every cyclist.

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

Road cycling in Sleepy Hollow features a diverse landscape of rolling hills, lush forests, and scenic views of the Hudson River. You'll encounter varied terrain, from gentle stretches along historic paths like the Old Croton Aqueduct Trail to routes with significant elevation gain in the rolling hills.

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

Yes, Sleepy Hollow offers family-friendly cycling options. The Old Croton Aqueduct Trail, for instance, provides gentle stretches along a historic path suitable for both walking and cycling. The Westchester RiverWalk also offers accessible riverside paths with beautiful views.

What are some popular road cycling routes in the Sleepy Hollow area?

Local road cyclists highly rate routes such as the New Croton Reservoir Loop, which offers stunning views of the New Croton Dam, and the Pine Bridge Monument – Quiet resting spot loop from Tarrytown. The 9W Market – Climb up to Alpine loop also features varied terrain and notable climbs.

What scenic views or landmarks can I see while cycling in Sleepy Hollow?

Many routes offer breathtaking views of the Hudson River, especially from locations like Kingsland Point Park and along the Westchester RiverWalk. You can also pass by historic sites such as the Sleepy Hollow Cemetery and the reconstructed Headless Horseman Bridge, or enjoy the natural beauty of Rockefeller State Park Preserve.

Is there parking available for road cyclists near the trails?

While specific parking areas for each route vary, many popular starting points for cycling routes in Sleepy Hollow, such as those near Tarrytown or within Rockefeller State Park Preserve, typically offer parking facilities. It's advisable to check specific route details for the most convenient parking options.

Can I reach Sleepy Hollow's cycling trails using public transport?

Yes, Sleepy Hollow is accessible via public transport. The Metro-North Railroad's Hudson Line serves Tarrytown, which is adjacent to Sleepy Hollow and provides convenient access to the area's cycling routes and attractions. Many trains allow bicycles onboard, though restrictions may apply during peak hours.

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

The best time for road cycling in Sleepy Hollow is generally during the spring, summer, and fall months. These seasons offer pleasant weather, vibrant foliage, and comfortable temperatures for exploring the region's diverse terrain and scenic beauty. Autumn, in particular, is renowned for its stunning fall colors.

Are there any long-distance road cycling routes in Sleepy Hollow?

Sleepy Hollow is part of a larger network of cycling paths. The Old Croton Aqueduct Trail, for example, spans 26.2 miles from Croton-on-Hudson to the Bronx, offering a significant distance for cyclists looking for longer rides. Other routes, like the Pine Bridge Monument loop, also provide substantial mileage.

What do other road cyclists say about their experience in Sleepy Hollow?

The road cycling routes around Sleepy Hollow are highly rated by the komoot community, with an average score of 4.6 stars from over 145 reviews. Cyclists often praise the diverse terrain, the stunning Hudson River views, and the blend of historic and natural attractions along the routes.

Are there any challenging road cycling routes for experienced riders?

Yes, Sleepy Hollow offers routes with significant elevation gain and varied terrain suitable for experienced riders. Options like the 9W Market – Climb up to Alpine loop from Tarrytown feature notable climbs and more demanding sections, providing a good challenge for advanced cyclists.

Can I find circular road cycling routes in the Sleepy Hollow area?

Many of the popular road cycling routes in Sleepy Hollow are designed as loops, allowing cyclists to start and end at the same point. Examples include the New Croton Reservoir Loop and the Pine Bridge Monument – Quiet resting spot loop, which offer comprehensive tours of the area's highlights.

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