The best walks and hikes around Sleepy Hollow
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Hiking around Sleepy Hollow, New York, is characterized by its location within the scenic Hudson River Valley, offering views of the Catskill and Taconic Mountains. The terrain features rolling hills, tranquil riverside paths along the Pocantico River, and extensive woodland trails. Many routes are located within the Rockefeller State Park Preserve, providing a mix of crushed-stone carriage roads and dirt trails through varied ecosystems. The area's natural features include open meadows, dense forests, and wetlands, catering to diverse outdoor activities.
…Last updated: May 12, 2026
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8
hikers
8.86km
02:36
270m
220m
Embark on the Terra Linda Ridge and 680 Trail for a moderate hike spanning 5.5 miles (8.9 km). You will ascend 893 feet (272 metres) over approximately 2 hours and…
5
hikers
11.2km
03:36
480m
480m
Hike the Loma Alta Peak Trail for a moderate challenge, panoramic Bay Area views, and seasonal wildflowers in Marin County.
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3
hikers
23.1km
07:04
770m
830m
This difficult 14.4-mile hiking loop in Loma Alta Open Space Preserve offers challenging climbs and expansive views of San Francisco.
16
hikers
7.89km
02:25
270m
270m
Hike the moderate 4.9-mile Old Railroad Grade loop in Loma Alta Open Space Preserve, featuring 875 feet of elevation gain and panoramic view
6
hikers
3.57km
01:08
130m
130m
Discover the Ridgewood Fire Road and Cemetery Fire Road Loop, an easy hike that offers a refreshing escape into nature. As you follow the Ridgewood Fire Road, you will first…
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Tips from the Community
Loma Alta literally translates to "high hill" and is the highest point in the Loma Alta Open Space Preserve. A few different dirt roads and trails lead to the bald summit that looks over the surrounding hillsides.
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Sorich Ranch Park is a great place to experience the natural beauty of the San Anselmo hills. There is a small parking lot and plenty of street parking nearby, with no day use/parking fee required to explore the grounds. There are picnic benches and tables with hiking trails that lead off in several directions and vary for options on whichever level of hike you choose. Several points in the Park boast stunning views and plenty of opportunities to take great photos of Mt. Tamalpais, Bald Hill and the Seminary.
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At 1592 feet, Loma Alta is one of the highest points in Marin. For a less strenuous excursion, from the lower Loma Alta Open Space Preserve entrance on the Fairfax side to the White Hill entrance, Old Railroad Grade Fire Road runs along the lower perimeter of the 509-acre preserve. In rainy season, see Fairfax Falls cascading 25 feet. https://www.marincountyparks.org/parkspreserves/preserves/loma-alta
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Enjoy heavenly Bay Area views, especially at sunrise and sunset: Here you can leave the gradual former railroad grade and take the extremely steep Sunrise Fire Road trail to the summit. At 1592 feet, Loma Alta is one of the highest points in Marin. https://www.marincountyparks.org/parkspreserves/preserves/loma-alta
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White Hill Trail crosses under Brown Bridge and then climbs steeply to link Loma Alta Preserve ( https://www.marincountyparks.org/parkspreserves/preserves/loma-alta ) with White Hill Preserve ( https://www.marincountyparks.org/parkspreserves/preserves/white-hill ), which further links up with Cascade Canyon Preserve, and Gary Giacomini Preserve.
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Steep switchbacks single track to hike down into the canyon
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To avoid the traffic when riding up (or down) White Hill, the highest elevation along Sir Francis Drake Boulevard from Fairfax, the old railroad grade is a more gradual, mostly smooth gravel trail alternative.
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Rolling hills and mountains as far as the eye can reach!
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Frequently Asked Questions
Are there any easy, family-friendly hikes in Sleepy Hollow?
Yes, the area is well-suited for family outings. The trails within Rockefeller State Park Preserve are particularly good for families, featuring wide, crushed-stone carriage roads that are easy to walk. The paths around Swan Lake and through Rockwood Hall offer gentle terrain and beautiful scenery.
Can I bring my dog on the trails?
Many trails in the Sleepy Hollow area are dog-friendly, provided your dog is kept on a leash. The expansive carriage road system in Rockefeller State Park Preserve is a popular choice for dog walkers, offering plenty of space. Always check specific park regulations before you go.
How do I get to the Sleepy Hollow trails using public transport from NYC?
You can take the Metro-North Railroad's Hudson Line from Grand Central Terminal to Tarrytown station. From there, it's a short walk or taxi ride to the entrances of major trail networks like the Old Croton Aqueduct Trail and Rockefeller State Park Preserve.
What are the best trails for seeing fall foliage?
For impressive autumn colors, head to the trails within Rockefeller State Park Preserve. The paths leading up to Eagle Hill are particularly rewarding, offering panoramic views over the Hudson River and the Palisades, which are spectacular during the fall season.
Are there any circular walks available?
Yes, many of the trails are designed as loops. For a moderately challenging circular route, consider the White Hill and B-17 crash loop — White Hill Preserve. It offers a varied experience through different types of terrain.
What is the Old Croton Aqueduct Trail like?
The Old Croton Aqueduct Trail is a unique, mostly flat linear park that follows the path of a 19th-century aqueduct. It's a historical walk that passes through woodlands and villages, offering a different perspective than the park trails. It's great for an easy, long-distance walk.
Where can I find good views of the Hudson River?
The Rockwood Hall section of the Rockefeller State Park Preserve offers grand vistas of the Hudson River and the Palisades. The trails here wind through open, grassy fields and past the foundations of the former Rockefeller estate, providing stunning, unobstructed views.
Are there any particularly historic trails?
Absolutely. Besides the Old Croton Aqueduct, many trails in Rockefeller State Park Preserve follow the historic carriage roads built by the Rockefeller family. You can also hike past historic stone bridges and features like Spook Rock, immersing yourself in the area's rich past.
What do other hikers enjoy about the trails around Sleepy Hollow?
The area is highly rated by the komoot community, with an average score of 4.9 stars. Reviewers often praise the well-maintained carriage roads, the beautiful scenery along the Pocantico River, and the peaceful atmosphere of the woodlands.
Is there a shorter hike I can do if I'm pressed for time?
For a quick but rewarding hike, the Sorich & Tomahawk Trail loop — Sorich Ranch Park is a great option. It's a relatively short loop that still provides a good sense of the local landscape.
Where are the main places to start a hike in the area?
The most popular starting point is the main entrance to Rockefeller State Park Preserve, which is highly regarded by locals and offers access to dozens of trails. Other key access points include trailheads for the Old Croton Aqueduct State Historic Park and the trails at Rockwood Hall.
Are there any paved trails suitable for strollers or wheelchairs?
While most of the park trails are crushed stone, the paved path at Tarrytown Lakes Park is an excellent option. It follows a former railroad bed, making it flat and accessible. The nearby Scenic Hudson RiverWalk Park at Tarrytown also offers paved surfaces with beautiful river views.
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