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.
Last updated: May 5, 2026
39
runners
33.5km
03:35
530m
530m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
29
runners
23.3km
02:27
160m
160m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Sign up for free
5.0
(1)
23
runners
10.6km
01:08
120m
120m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
17
runners
15.9km
01:43
250m
250m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
10
runners
9.31km
01:00
130m
130m
Moderate run. 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
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.
0
0
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.
0
0
Beautiful little lake at the park entrance
1
0
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.
0
0
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.
0
0
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.
1
0
"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.
0
0
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.
0
0
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.


Browse the best Running Trails & Routes in other regions.