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Running Trails
United States
New York
Westchester County

Sleepy Hollow

The best running trails around Sleepy Hollow

4.8

(16)

1,211

runners

15

runs

Jogging around Sleepy Hollow offers diverse landscapes, from historic trails to picturesque waterfronts along the Hudson River. The region features varied terrain, including well-maintained crushed-stone paths, wooded trails, and paved sections. Rolling hills and natural elements like the Pocantico River and several lakes add to the scenic beauty. This environment provides a compelling setting for runners of all levels.

Best jogging routes around Sleepy Hollow

  • The most popular jogging route is Triple Arch Bridge – Foundation Ruins loop from Tarrytown

Last updated: May 5, 2026

39

runners

#1.

Swan Lake – Pocantico Falls loop from Philipse Manor

33.5km

03:35

530m

530m

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Tips from the Community

oliviakellis
May 28, 2024, Painters Point

At Painters Point, perched 102 feet high on the Mario M. Cuomo Zee Bridge, find inspiration in the majestic Hudson River scenery. A unique bronze and wood structure frames views of the river and Hook Mountain, inviting reflection and appreciation. Join the long legacy of artists moved by the Hudson's beauty as you stand on this elevated viewpoint.

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Perched 125 feet high on the bridge path, the Tides of Tarrytown overlook offers a unique perspective on the village's rich history and evolving shoreline. The timber-clad bench doubles as a panoramic viewing platform, allowing you to absorb the northern vista of Tarrytown and the southern skyline of New York City.

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Beautiful little lake at the park entrance

Translated by Google

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Perched 125 feet high on the bridge path, the Tides of Tarrytown overlook offers a unique perspective on the village's rich history and evolving shoreline. The timber-clad bench doubles as a panoramic viewing platform, allowing you to absorb the northern vista of Tarrytown and the southern skyline of New York City.

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Will
December 29, 2023, Philipsburg Manor

Philipsburg Manor is a very interesting historic site and museum, focusing on the lives of enslaved Africans in the 18th century, and featuring a reconstructed water-powered gristmill.

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oliviakellis
December 17, 2023, Painters Point

At Painters Point, perched 102 feet high on the Mario M. Cuomo Zee Bridge, find inspiration in the majestic Hudson River scenery. A unique bronze and wood structure frames views of the river and Hook Mountain, inviting reflection and appreciation. Join the long legacy of artists moved by the Hudson's beauty as you stand on this elevated viewpoint.

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oliviakellis
December 16, 2023, Hulda's Hut

"Hulda the Witch" was likely a misunderstood healer who lived on this site long ago. While her true story remains a mystery, local legends portray her as an intriguing figure in the area's history. The recreation here was designed by the Preserve to share her tale and highlight the folklore surrounding this location.

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oliviakellis
December 16, 2023, Pocantico Falls

This impressive waterfall, the largest in the Preserve, transforms with the seasons - from a thundering cascade after heavy rains to a trickling stream in times of drought. In winter, it freezes into brilliant ice formations that sparkle in the sunshine, showcasing the falls' wild and compelling splendor through all its guises.

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Frequently Asked Questions

How many running routes are available in Sleepy Hollow?

Sleepy Hollow offers a wide variety of running experiences, with over 100 routes documented on komoot. These range from easy paths to more challenging trails, catering to all fitness levels.

Are there running trails suitable for beginners or those looking for an easy jog?

Yes, Sleepy Hollow has options for all abilities. While many routes feature rolling hills, you can find easier sections, particularly along the Hudson River waterfront. For a moderate option, consider the Tarrytown Light – Tarrytown Village Hall loop from Tarrytown, which is just under 10 miles and offers scenic views.

What kind of terrain can I expect on the running trails in Sleepy Hollow?

The region boasts diverse terrain, perfect for varied workouts. You'll find well-maintained crushed-stone paths, wooded trails, and paved sections. Many routes, especially within Rockefeller State Park Preserve, utilize historic carriage roads, providing a smooth surface through natural landscapes.

Are there any family-friendly running routes in Sleepy Hollow?

Absolutely. Many of the trails, particularly the wider carriage roads in areas like Rockefeller State Park Preserve, are suitable for families. These paths often wind through meadows and forests, offering a pleasant and safe environment for a family jog or walk. The Scenic Hudson Riverwalk also provides flat, accessible sections.

Can I bring my dog on the running trails?

Many trails in Sleepy Hollow are dog-friendly, especially those in parks and preserves. It's always best to check specific park regulations, but generally, dogs on a leash are welcome. The extensive carriage trails of Rockefeller State Park Preserve are a popular choice for runners with canine companions.

Are there any running routes with historical landmarks or points of interest?

Sleepy Hollow is rich in history. The Triple Arch Bridge – Foundation Ruins loop from Tarrytown takes you through historic areas. You can also explore sections of the Old Croton Aqueduct Trail, a historic 26.2-mile recreational path. For a unique experience, the 90-acre Sleepy Hollow Cemetery offers rolling hills and peaceful streams, making for a serene jog amidst historical gravestones.

What are some scenic spots or natural features to look out for while running?

Sleepy Hollow offers stunning natural beauty. The Hudson River waterfront provides breathtaking views of the river and the Tappan Zee Bridge. You'll also encounter natural elements like the Pocantico River and several lakes, including Tarrytown Lakes, which are home to diverse wildlife. The Swan Lake – Pocantico Falls loop from Philipse Manor specifically highlights some of these natural gems.

Are there any long-distance running options for experienced runners?

Yes, for those seeking a longer challenge, the region offers extensive trails. The Old Croton Aqueduct Trail stretches for 26.2 miles, providing a marathon-distance option. Rockefeller State Park Preserve also features over 50 miles of carriage trails, allowing for extended runs through varied landscapes. The Swan Lake – Pocantico Falls loop from Philipse Manor is a difficult 20.8-mile path for a substantial workout.

Where can I find parking for the running trails in Sleepy Hollow?

Parking is generally available at key access points for popular running areas. For instance, Rockefeller State Park Preserve has designated parking areas. For routes starting in Tarrytown or Sleepy Hollow villages, public parking lots are often available, though it's advisable to check local signage for specific regulations and fees.

Is public transport an option to reach the running routes?

Sleepy Hollow and Tarrytown are accessible via public transport, primarily through Metro-North Railroad from New York City. Once in the villages, many trailheads, especially those along the waterfront or connecting to the Old Croton Aqueduct Trail, are within walking distance or a short local bus ride.

What do other runners enjoy most about jogging in Sleepy Hollow?

The running routes in Sleepy Hollow are highly rated by the komoot community, with an average score of 4.6 stars. Runners frequently praise the diverse landscapes, from the scenic Hudson River waterfront to the peaceful, well-maintained carriage trails of Rockefeller State Park Preserve. The mix of historic ambiance and natural beauty makes for a truly unique running experience.

Are there any loop running trails in the area?

Many of the popular running routes in Sleepy Hollow are designed as loops, offering a convenient way to explore without retracing your steps. Examples include the Triple Arch Bridge – Pocantico Falls loop from Rockefeller State Park Preserve and the Triple Arch Bridge – Foundation Ruins loop from Tarrytown, providing varied scenery on circular paths.

Are there any cafes or places to grab a refreshment near the running trails?

Yes, the villages of Sleepy Hollow and Tarrytown offer various cafes and eateries where you can refuel after your run. For example, 9W Market is a popular spot. Many routes, especially those starting or passing through the village centers, are conveniently located near these amenities.

Most popular routes around Sleepy Hollow

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