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.
Last updated: July 8, 2026
5.0
(7)
405
riders
80.2km
03:50
980m
980m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(3)
162
riders
79.0km
03:58
880m
880m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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284
riders
86.1km
03:51
750m
750m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(3)
99
riders
46.6km
02:40
1,040m
1,040m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
4.8
(4)
363
riders
52.8km
02:48
930m
930m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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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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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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