4.6
(391)
3,938
riders
5
rides
No traffic touring cycling routes around Sleepy Hollow navigate a landscape characterized by rolling hills, scenic riverfronts, and diverse terrain. The region features the Hudson River waterfront and the serene Pocantico River valley, offering varied natural settings. A network of dedicated pathways and historic carriage roads provides opportunities for touring cyclists to explore the area's natural beauty.
Last updated: November 6, 2026
9
riders
14.0km
01:31
460m
460m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
9
riders
48.5km
04:27
1,150m
1,150m
Hard bike ride. Very good fitness required. Mostly paved surfaces.

5.0
(2)
6
riders
30.3km
03:08
860m
860m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
6
riders
37.8km
04:05
1,340m
1,340m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
6
riders
37.8km
04:05
1,340m
1,340m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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The Dixie Schoohouse dates back to 1864, it has been in continuous use since its construction, making it the oldest in Marin County. It was listed on the National Register of Historic Places in 1972.
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This town, nestled in the forested hills among unspoiled open space in Marin County, is a nice respite from the large nearby metropolis. It is a quirky, hip place with a small-town vibe filled with restaurants, music venues, and independent shops. Fairfax is home to many musicians who live here, and on any given night, you can find live music featuring local and national touring acts jamming in a relaxed, casual atmosphere. It has a very cycle-friendly culture, and be sure to take the time to visit the Museum of Bicycling while you are here!
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Historic 1864s one-room school, the oldest in Marin County
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Get off the highway and help promote safe bikeways in the San Geronimo Valley! School trail is mostly well-compacted gravel, a great alternative to parallel but out of sight and danger of busy Sir Francis Drake Boulevard. Currently only this short section between Forest Knolls and Lagunitas School. Great start people, extend the trail !
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Beautiful grove of tall redwood trees along a small streambed along Bolinas and Park Roads in downtown Fairfax.
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There are over 50 dedicated no-traffic touring cycling routes around Sleepy Hollow. These routes are carefully curated to provide a safe and enjoyable experience away from vehicular traffic, allowing you to fully immerse yourself in the region's natural beauty.
Yes, Sleepy Hollow offers a good selection of easy, no-traffic touring cycling routes perfect for beginners and families. There are 12 routes specifically rated as easy, often following flat, well-maintained paths like sections of the Old Croton Aqueduct Trail. These routes provide a gentle introduction to the area's scenic landscapes without significant elevation changes.
The car-free touring bike routes in Sleepy Hollow offer a diverse range of terrain. You'll find everything from paved paths along the Hudson River waterfront to well-maintained gravel sections on historic carriage roads and trails. The region's rolling hills mean some routes will include moderate climbs, but many car-free options prioritize flatter, more accessible surfaces.
Many car-free touring routes in Sleepy Hollow offer stunning views and access to local attractions. You can enjoy picturesque vistas of the Hudson River, including the Tappan Zee Bridge. Highlights like the Cal Park Tunnel & Pathway provide unique cycling experiences, while the China Camp State Park Village offers a historical stop. For natural beauty, consider routes near Mount Tamalpais — East Peak or the The Big Rock - Skywalker Ranch.
Yes, several no-traffic touring cycling routes in Sleepy Hollow are designed as loops, allowing you to start and end at the same point without retracing your steps. While specific named loops are part of the broader network, routes often combine sections of the Old Croton Aqueduct Trail with other car-free paths to create circular journeys through the scenic Hudson River Valley.
The best time for no-traffic touring cycling in Sleepy Hollow is typically spring, early summer, and fall. During these seasons, the weather is generally mild and pleasant, and the natural scenery, from blooming flowers to vibrant autumn foliage, is at its peak. Summer can also be enjoyable, though it can get warm, while winter may present challenges with snow and ice on some trails.
Yes, you can find places to stop for refreshments. While many car-free trails prioritize natural immersion, some routes pass through or near charming towns where cafes and eateries are available. For example, the Splitrock Tap & Wheel is a notable highlight near some cycling routes, offering a convenient stop for cyclists.
The komoot community highly rates touring cycling in Sleepy Hollow, with an average score of 4.5 stars. Reviewers often praise the region's unique blend of historical significance and natural beauty, particularly the peaceful, car-free paths that offer stunning views of the Hudson River and access to charming villages. The well-maintained trails and diverse scenery are frequently highlighted as major draws.
Absolutely. Sleepy Hollow is rich in both history and natural beauty. Many no-traffic routes, such as those incorporating the Old Croton Aqueduct Trail, are historical paths themselves. You can also find routes that lead to or pass by landmarks like the Marin Museum of Bicycling or natural features like the Bon Tempe Dam, offering a blend of outdoor activity and cultural exploration.
While the focus is on no-traffic, some routes offer a significant challenge. For instance, the Loma Alta Summit – 680 Trail loop from Sleepy Hollow is rated as difficult, featuring substantial elevation gain over its 13.6 km distance. Another challenging option is the Fairfax Falls 🌊 – Fairfax loop from Sleepy Hollow, which covers over 30 km with considerable climbing, providing a robust workout for experienced riders seeking car-free adventures.
Parking availability varies by trailhead. Many popular access points for trails like the Old Croton Aqueduct Trail or sections leading to Rockefeller State Park Preserve offer designated parking areas. It's advisable to check specific route details on komoot or local park websites for precise parking information before you head out. For more details on Rockefeller State Park Preserve, you can visit visitsleepyhollow.com.


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