4.8
(35)
499
hikers
87
hikes
Hiking around Pleasantville offers access to a diverse landscape, primarily centered around the Rockefeller State Park Preserve. This region features rolling meadows, historic carriage roads, and extensive woodlands. Hikers can experience varied terrain, from gentle paths to trails with moderate elevation changes, all within the scenic Hudson Valley. The area provides a blend of natural beauty and well-maintained routes suitable for outdoor exploration.
Last updated: May 1, 2026
7
hikers
6.01km
01:37
80m
70m
Embark on an easy hike through the Brook, David and Swan Lake Loop, a 3.7-mile (6.0 km) route that offers a gentle escape into nature. You will experience a mix…
5.0
(1)
5
hikers
8.09km
02:12
120m
100m
Hike the 5.0-mile Buttermilk Hill to Reservoir Loop in Rockefeller State Park Preserve, a moderate route with varied terrain and historic ca

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2
hikers
11.3km
03:06
190m
190m
Hike the moderate 7.0-mile Overlook and Ash Tree Loop in Rockefeller State Park Preserve, featuring shaded forests and Pocantico Falls.
2
hikers
4.67km
01:17
80m
80m
Hike the easy 2.9-mile Gedney Park Red Trail Loop through scenic woodlands, wetlands, and varied terrain in Westchester County, New York.
1
hikers
1.73km
00:28
20m
20m
Hike the easy 1.1-mile Blue Trail in Whippoorwill Park, a quick 28-minute route with 80 feet of elevation gain.
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Beautiful little lake at the park entrance
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This plaque from 1833 commemorates the 200th anniversary of the Buttermilk Hill triangulation station established by the US Geological Survey. This station is recognized as the oldest triangulation point in America. The actual survey marker is located about half a mile west of where this commemorative plaque stands.
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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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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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This large glacial erratic, measuring 20 feet high and 65 feet in circumference, was likely transported here over 10,000 years ago by a glacier originating in the Arctic Circle region. After a long journey south, it was deposited in what is now the Preserve, making it one of the largest glacial erratics found in the Hudson River Valley.
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This plaque from 1833 commemorates the 200th anniversary of the Buttermilk Hill triangulation station established by the US Geological Survey. This station is recognized as the oldest triangulation point in America. The actual survey marker is located about half a mile west of where this commemorative plaque stands.
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Pleasantville offers a wide variety of hiking experiences, with over 60 routes available. These trails cater to different preferences, from gentle strolls to more challenging hikes, primarily within the Rockefeller State Park Preserve and surrounding areas.
Yes, Pleasantville is well-suited for easy hikes, with over 40 routes classified as easy. The Rockefeller State Park Preserve features historic carriage roads with gentle grades, perfect for relaxed walks. An example of an easy route is the Raven's Rock Loop – Rockefeller State Park Preserve, which is about 4.2 miles long.
Hiking in Pleasantville offers diverse scenery, characterized by rolling meadows, dense woodlands, and historic carriage roads. Many trails provide picturesque views of the Hudson Valley, especially within the Rockefeller State Park Preserve. You'll encounter forests, open fields, wetlands, and opportunities for birdwatching throughout the year.
Yes, many of the trails in Pleasantville are designed as circular routes, allowing you to start and end at the same point. Popular examples include the Glacial Erratic via Brother's Path loop and the Swan Lake Loop, both within the Rockefeller State Park Preserve.
Absolutely. The extensive network of trails, particularly the wide and well-maintained carriage roads in the Rockefeller State Park Preserve, are ideal for families. Their gentle grades and scenic beauty make them suitable for all ages and fitness levels, offering a pleasant outdoor experience for everyone.
Many trails in the Pleasantville area, including those within the Rockefeller State Park Preserve, are dog-friendly. It is generally required that dogs be kept on a leash to protect wildlife and ensure a pleasant experience for all visitors. Always check specific park regulations before your visit.
Beyond the trails themselves, Pleasantville's surroundings offer several points of interest. You can explore the Kensico Reservoir or the Tarrytown Reservoir, both providing scenic views. The South County Trailway and Nyack River Trail also offer additional outdoor exploration opportunities.
Pleasantville offers beautiful hiking experiences throughout the year. Spring brings vibrant blooms, summer provides lush greenery, and autumn transforms the landscape with stunning fall foliage. Even winter hiking can be rewarding, with serene, snow-covered trails offering a different perspective of the natural beauty.
Yes, many trails in Pleasantville remain accessible for winter hiking, offering a peaceful and picturesque experience. The wide carriage roads of the Rockefeller State Park Preserve are particularly suitable for winter walks, often providing clear paths even after light snowfall. Be sure to dress warmly and wear appropriate footwear.
Parking is generally available at the main entrances to the Rockefeller State Park Preserve and other trailheads in the Pleasantville area. Specific parking instructions and fees (if any) are usually posted at the park entrances or on their official websites. It's advisable to check ahead, especially during peak seasons.
Yes, the North County Trailway passes through the broader Pleasantville area. This accessible path, originally a railway line, offers a relatively flat and well-maintained surface, making it suitable for hiking, jogging, and cycling, and is a great option for longer, less strenuous walks.
The hiking trails around Pleasantville are highly regarded by the komoot community, with an impressive average rating of 4.8 stars from over 30 reviews. Hikers frequently praise the well-maintained paths, the beautiful and varied scenery, and the peaceful atmosphere of the Rockefeller State Park Preserve.


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