Sleepy Hollow is a region in New York known for its blend of history and natural landscapes, situated on the east bank of the Hudson River. The area features rolling hills, lush forests, and the Pocantico River Valley, providing diverse terrain for outdoor pursuits. This geography makes Sleepy Hollow suitable for several sports like hiking, road cycling, jogging, mountain biking, and more. The Rockefeller State Park Preserve, with its extensive carriage roads and trails, is a central feature for outdoor…
84
Routes
4.6
(60)
Average rating
2052
People visited

5.0
(1)
15
hikers
5.84km
01:43
180m
170m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

5.0
(1)
8
hikers
8.86km
02:36
270m
220m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

4
hikers
11.2km
03:36
480m
480m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

3
hikers
23.1km
07:04
770m
830m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
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5.0
(6)
406
riders
80.2km
03:50
980m
980m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

5.0
(3)
168
riders
79.2km
03:53
880m
880m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

5.0
(3)
99
riders
46.6km
02:40
1,040m
1,040m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

5.0
(4)
90
riders
37.7km
02:06
810m
810m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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10
runners
11.9km
01:38
400m
400m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

11.0km
01:46
680m
670m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

15.2km
02:08
660m
660m
Hard run. Very good fitness required. Mostly accessible paths. Some sure footedness required.

5.0
(1)
23
runners
26.8km
03:39
1,060m
1,060m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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16
riders
29.8km
02:38
640m
640m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

4.8
(5)
31
riders
35.3km
03:51
1,150m
1,150m
Hard mountain bike ride. Very good fitness required. Suitable for all skill levels.

5.0
(1)
38
riders
41.6km
04:05
1,070m
1,070m
Hard mountain bike ride. Very good fitness required. Suitable for all skill levels.

5.0
(1)
15
riders
13.3km
01:17
340m
340m
Moderate mountain bike ride. Good fitness required. Advanced riding skills necessary.
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51
riders
27.3km
02:31
550m
550m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
28
riders
34.4km
02:44
450m
450m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

17
riders
42.7km
02:35
300m
300m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.0
(1)
16
riders
45.0km
02:54
560m
560m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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4.0
(2)
35
riders
65.9km
04:42
1,010m
1,010m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

3.0
(1)
9
riders
38.6km
03:35
950m
940m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

9
riders
52.5km
05:00
1,510m
1,510m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
14
riders
32.2km
02:34
460m
460m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Sleepy Hollow offers a variety of outdoor activities, including Hiking, Road cycling, Jogging, Mountain biking, Touring cycling, and Gravel biking. The region's landscape features rolling hills, forests, and views of the Hudson River, providing diverse terrain for these pursuits.
Sleepy Hollow is a popular destination on komoot, with more than 18,000 visitors sharing their experiences. The region's 18 routes have an average rating of 4.69 out of 5 stars, based on over 800 ratings.
Sleepy Hollow offers numerous hiking opportunities, primarily within the Rockefeller State Park Preserve, which features over 50 miles of trails. The Old Croton Aqueduct Trail is another historic pathway suitable for walking and hiking. The Sleepy Hollow Cemetery also provides a scenic setting for walks.
Yes, many trails in Rockefeller State Park Preserve are former carriage roads, offering varied terrain suitable for different fitness levels, including easy walks. For more options, consult the Easy hikes around Sleepy Hollow guide.
Sleepy Hollow offers road cycling routes with rolling hills and scenic views of the Hudson River. Popular options include the New Croton Reservoir Loop and routes from Tarrytown like The Pine Bridge Monument loop. More details can be found in the Road Cycling Routes around Sleepy Hollow guide.
Many of the hiking trails in Sleepy Hollow are suitable for jogging, especially those in Rockefeller State Park Preserve and the Old Croton Aqueduct Trail. These routes offer scenic paths for runners. The Running Trails around Sleepy Hollow guide provides specific options.
Mountain biking opportunities exist in Sleepy Hollow, utilizing the extensive carriage roads within Rockefeller State Park Preserve. Some specialized singletrack trails are also available in the wider region. The MTB Trails around Sleepy Hollow guide offers more information.
Sleepy Hollow is characterized by its location on the Hudson River, offering waterfront views. The Pocantico River Valley runs through Rockefeller State Park Preserve and Sleepy Hollow Cemetery. The Rockefeller State Park Preserve itself is a 1,400-acre area with rolling hills and forests.
Yes, komoot offers several guides for Sleepy Hollow, including Hiking around Sleepy Hollow, Road Cycling Routes around Sleepy Hollow, and MTB Trails around Sleepy Hollow. Guides for Easy hikes, Running, Cycling, and Gravel biking are also available.
The official website for the Village of Sleepy Hollow, New York, is www.sleepyhollowny.gov. This site provides general information about the village.
For general inquiries regarding Sleepy Hollow, the Village Clerk can be reached at (914) 366-5106. The Greater Sleepy Hollow Tarrytown Chamber of Commerce can also be contacted at (914) 631-1705 for tourism-related information.

