4.5
(343)
3,721
riders
165
rides
Touring cycling around Sleepy Hollow, New York, offers a diverse landscape characterized by the Hudson River Valley and dedicated multi-use trails. The region features relatively flat, hard-packed dirt pathways like the Old Croton Aqueduct Trail, alongside paved road cycling routes with varied elevation gains around areas such as Rockefeller State Park Preserve. Cyclists can experience scenic river views and pass through historic estates and charming riverfront communities. The terrain provides options ranging from gentle linear paths to more challenging routes…
Last updated: July 4, 2026
1
riders
18.5km
01:29
330m
330m
Cycle the moderate 11.5-mile Cascade Drive & Iron Springs Road loop in Marin County, California, with 1089 feet of elevation gain.
14.5km
01:28
450m
450m
The White Hill and Blue Ridge Fire Roads Loop offers a dynamic touring cycling experience through Marin County's diverse landscapes. You'll pedal through pockets of California bay and coast live…

Sign up for free
50
riders
21.8km
02:01
440m
440m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
56
riders
47.4km
04:55
1,410m
1,410m
This challenging 29.4-mile (47.4 km) touring cycling loop from Fairfax takes you on a scenic adventure through the Mt. Tamalpais Watershed, offering 4615 feet (1407 metres) of elevation gain over…
5.0
(3)
32
riders
31.1km
02:09
560m
560m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
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.
1
0
Mount Tam East Peak offers some of the most majestic views north of the bay. From this vantage point, you can see all of Marin, along with Point Reyes to the north and Oakland and San Francisco to the south. The stunning panoramic vistas make the journey well worth the effort. There are restrooms and picnic tables, ideal for a snack or lunch while you capture some incredible photos.
0
0
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.
0
0
West of Lake Lagunitas, Bon Tempe Lake is a reservoir managed by Marin Municipal Water District. It features striking scenery, with lush trees, clear water, and a peaceful atmosphere.
0
0
At this point on Sky Oaks Road, there is a junction with Shaver Grade Road, which connects with a dense network of trails and dirt roads near Bald Hill in the Mount Tamalpais State Park. From here, you can continue on the paved Sky Oaks Road or go arond the gate on to the gravel Shaver Grade Road.
0
0
This bikeway offers a better alternative to the much busier Center Boulevard, which does not have a shoulder and an even better route than the Sir Francis Drake Blvd highway. Lansdale and San Anselmo Avenues are quiet residential streets that run parallel and provide a pleasant passage through town away from busy traffic.
1
0
Mount Tamalpais State Park is a majestic area in the heart of Marin County, with sweeping hillsides covered in fantastic redwood forest, open grasslands, sturdy chaparral, and wooded oaklands. The views from Mount Tampais boast breathtaking vistas of the Pacific Ocean, San Francisco Bay and City, the Marin County Hills, Mount Diablo, and the East Bay. You can even see the Farallon Islands, 25 miles out to sea. If you're lucky, you can catch an occasional glimpse of the snow-capped Sierra Nevada Mountain Range, nearly 150 miles away. The Park is a haven for cyclists, hikers, wildlife watchers, or those who wish to find a beautiful spot for an afternoon picnic.
0
0
There are over 150 touring cycling routes around Sleepy Hollow, offering a diverse range of experiences. These include 38 easy routes, 65 moderate routes, and 54 difficult routes, catering to various skill levels.
Sleepy Hollow's touring cycling routes feature a varied landscape, from relatively flat, hard-packed dirt pathways like sections of the Old Croton Aqueduct Trail to paved road cycling routes with significant elevation gains, especially around areas such as Rockefeller State Park Preserve. You'll encounter rolling hills, lush forests, and scenic views of the Hudson River.
Yes, for a gentler experience, the Old Croton Aqueduct Trail offers a relatively flat and historic path suitable for families. While some trails in Rockefeller State Park Preserve are restricted for bikes, the preserve's general tranquility and natural setting are appealing. For specific easy routes, consider options like the Corte Madera Pathway – Corte Madera - Larkspur Path loop from San Anselmo, which is rated as easy.
Many routes offer stunning vistas of the Hudson River. The region is characterized by rolling hills and forested sections. You can also find highlights like Phoenix Lake and Alpine Dam, which are part of the 'Lakes around Sleepy Hollow' guide. Rockwood Hall, within Rockefeller State Park Preserve, provides panoramic views of the Hudson River.
Yes, for longer rides, the New Croton Reservoir Loop is a popular moderate trail for road cyclists, spanning 39.9 miles (64.2 km). Another option is "The Pine Bridge Monument – Quiet resting spot loop from Tarrytown," a 54.7-mile path. The Old Croton Aqueduct Trail itself extends 26.2 miles from Croton-on-Hudson to the Bronx, offering a substantial linear route.
The area is highly rated by the komoot community, with an average score of 4.6 stars from over 170 reviews. Reviewers often praise the diverse terrain, scenic river views, and the mix of historic charm with natural beauty. Over 3700 touring cyclists have used komoot to explore Sleepy Hollow's varied terrain.
Yes, many routes are designed as loops. Examples include the challenging Lagoon Park in San Rafael – China Camp State Park loop from Sleepy Hollow, or the moderate Corte Madera - Larkspur Path – Corte Madera Pathway loop from Fairfax. The New Croton Reservoir Loop is also a well-known circular route.
The region is rich in history. The Old Croton Aqueduct Trail itself is a historic pathway. You can also explore areas near the Sleepy Hollow Cemetery, the Old Dutch Church, and the Pocantico River, which are tied to Washington Irving's legends. Kingsland Point Park, located on the Hudson River waterfront, is another scenic spot near the Sleepy Hollow Lighthouse.
Parking is available at various access points for popular trails. For instance, you can find parking near the Old Croton Aqueduct Trail and Rockefeller State Park Preserve. Specific parking details often depend on the exact starting point of your chosen route.
Yes, public transport can be used to access some routes. The Old Croton Aqueduct Trail, for example, passes through Sleepy Hollow and Tarrytown, which are accessible by public transportation. Check local transit schedules for the most convenient access points to your desired route.
While specific cafes directly on every route may vary, the towns of Sleepy Hollow and Tarrytown offer various establishments where you can refuel. For example, Splitrock Tap & Wheel is listed as a cafe highlight in the 'Bike Parks around Sleepy Hollow' guide, indicating cycling-friendly spots exist.


Browse the best Cycling routes in other regions.