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United States
New York
Westchester County

Pleasantville

The best walks and hikes around Pleasantville

4.8

(38)

512

hikers

86

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.

Best hiking trails around Pleasantville

  • The most popular hiking route is Glacial Erratic via Brother's Path loop — Rockefeller State Park Reserve, a 5.7 miles (9.2 km) trail that takes 2 hours 30 minutes to complete, leading through varied woodland and open areas.
  • Another top favourite among local hikers is Buttermilk Hill via Old Orchard Trail — Rockefeller State Park Preserve, a moderate 5.3 miles (8.5 km) path. This route features a mix of forest trails and open sections with some elevation gain.
  • Local hikers also love the Swan Lake Loop – Rockefeller State Park Preserve, a 2.5 miles (4.1 km) trail leading through woodlands and past Swan Lake, often completed in about 1 hour 5 minutes.
  • Hiking around Pleasantville is defined by rolling meadows, historic carriage roads, and dense woodlands, often with views of the Hudson Valley. The network offers options for various ability levels, from easy strolls to moderate hikes.
  • The routes in Pleasantville are highly rated by the komoot community with an average score of 4.8 stars from over 30 reviews. More than 400 hikers have used komoot to explore Pleasantville's varied terrain.

Last updated: June 28, 2026

7

hikers

#1.

Brook, David and Swan Lake Loop

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 of peaceful forested sections, open fields, and tranquil wetlands, all while gaining a modest 248 feet (76 metres) in elevation. This loop provides a refreshing outdoor experience that takes approximately 1 hour and 37 minutes to complete, perfect for a leisurely outing.

When planning your visit, you will find the trail primarily follows well-maintained crushed stone and gravel carriage roads. These wide paths were originally designed for horse-drawn travel, making them comfortable and accessible for hikers of all levels. Parking is generally available at Rockefeller State Park Preserve, providing convenient access to the trailhead.

This route stands out for its picturesque Swan Lake, a serene man-made body of water that forms a central feature of the preserve. The historic carriage roads themselves add a unique charm, inviting you to explore a landscape that blends natural beauty with a touch of the past.

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5.0

(1)

5

hikers

Hike the 5.0-mile Buttermilk Hill to Reservoir Loop in Rockefeller State Park Preserve, a moderate route with varied terrain and historic ca

Moderate
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3

hikers

Hike the moderate 7.0-mile Overlook and Ash Tree Loop in Rockefeller State Park Preserve, featuring shaded forests and Pocantico Falls.

Moderate

2

hikers

The Gedney Park Red Trail Loop offers a delightful escape into nature, guiding you through scenic woodlands filled with mature trees and younger growth. You'll traverse varied terrain, from gentle rocky ridges to tranquil valleys, and even skirt past wetlands and streams. It's a perfect spot to enjoy vibrant fall foliage or the lush greenery of spring, providing a peaceful experience for all.

Planning your visit to this easy 2.9-mile (4.7 km) hike is straightforward, as the park doesn't require permits or entrance fees. With only 270 feet (82 metres) of elevation gain, it's a gentle outing that takes about 1 hour and 17 minutes. The trail is open year-round, and parking is typically available at the trailhead, making it an easy choice for a spontaneous outdoor adventure.

This loop is part of a larger network of trails within Gedney Park, offering opportunities for longer explorations if you wish to combine it with sections of the Yellow, Blue, Purple, or Nature Trails. It's notably family-friendly and dog-friendly, allowing leashed dogs to accompany you, making it a popular choice for those looking for a relaxed outing with their loved ones.

Easy

1

hikers

1.73km

00:28

20m

20m

The Blue Trail offers a delightful, easy hiking experience, perfect for a quick nature fix. You'll wander along a mix of dirt paths, occasionally navigating small rocks and roots, through what feels like a serene forest setting. This route is designed for relaxation, allowing you to immerse yourself in the natural surroundings without any demanding climbs or technical terrain.

Planning your visit to the Blue Trail is straightforward, as it's an easy 1.1-mile (1.7 km) hike with only 80 feet (24 metres) of elevation gain, typically completed in about 28 minutes. There are no special permits or fees mentioned, making it an accessible option for a spontaneous outing. It's a great choice for families or anyone new to hiking, offering a gentle introduction to the trails.

While many "Blue Trails" can signify moderate difficulty in larger networks, this particular Blue Trail stands out for its approachable nature, making it a fantastic option for a leisurely walk. It provides a taste of the varied terrain often found on trails, from smooth dirt to slightly uneven ground, all within a manageable distance. This trail is a testament to how even short routes can offer a refreshing connection to the outdoors.

Easy
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Tips from the Community

Pierre Oscoeur
April 8, 2024, Swan Lake

Beautiful little lake at the park entrance

Translated by Google

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oliviakellis
September 12, 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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oliviakellis
September 12, 2023, Glacial Erratic

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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This is a beautiful 24-acre lake. A lovely spot!

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Frequently Asked Questions

How many hiking trails are available in Pleasantville?

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.

Are there easy hiking options in Pleasantville?

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.

What kind of scenery can I expect on Pleasantville's trails?

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.

Are there circular hiking routes in the area?

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.

Can I find family-friendly trails in Pleasantville?

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.

Are dogs allowed on the hiking trails in Pleasantville?

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.

What are some notable landmarks or attractions near the hiking trails?

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.

What is the best time of year to go hiking in Pleasantville?

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.

Are there options for winter hiking in Pleasantville?

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.

Where can I park when visiting the trails in Pleasantville?

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.

Are there any rail trails suitable for hiking in Pleasantville?

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.

What do other hikers say about the trails in Pleasantville?

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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