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United States
New York
Westchester County

Pleasantville

The best running trails around Pleasantville

By Fede from komoot

·

Updated May 30, 2026

If you've ever tried to plan jogging around Pleasantville, you know how overwhelming the options can be. With so many parks and trails, it's tough to tell which routes are genuinely worth your time and effort, and which are just filler. We get it – you want to hit the ground running on the best paths, not spend hours sifting through endless possibilities. That's where komoot comes in. Our community has mapped, run, and reviewed countless routes, and we've distilled that collective wisdom into a curated shortlist of the very best jogging routes in Pleasantville, saving you the guesswork.

Jogging in Pleasantville truly feels like stepping into a natural oasis. The landscape is defined by diverse woodlands, rolling meadows, and river valleys, with many routes following well-maintained crushed stone carriage roads and historic aqueduct paths. You'll find everything from gentle, relatively flat sections perfect for a relaxed pace to trails with moderate elevation changes that offer a good workout. The area's character is shaped by features like Swan Lake and the Pocantico River, and thanks to a mild climate, you can generally enjoy these trails year-round.

If you only have time for one, we'd point you towards the Pocantico Falls – Swan Lake loop from Rockefeller State Park Preserve. At 8.1 miles (13.1 km) with 590 feet (180 m) of elevation gain, this moderate route offers a fantastic taste of the region's varied terrain and scenic beauty, making it ideal for a rewarding morning run. For those looking to cover more ground on a classic trailway, the North County Trailway loop from Village of Briarcliff Manor is a solid choice, stretching 10.4 miles (16.7 km) with a gentler 210 feet (64 m) of climb. Ready to lace up? More than 400 runners have already explored Pleasantville's varied terrain with komoot, and now it's your turn.

If you only do 3 of these routes

  1. 1

    North County Trailway loop from Briarcliff Manor
  2. 2

    Pocantico Falls – Glacial Erratic loop from Rockefeller State Park Preserve
  3. 3

    Buttermilk Hill USGS Benchmark – Raven's Rock loop from Pleasantville

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

North County Trailway loop from Briarcliff Manor

16.7 km

60 m

Hard

Pocantico Falls – Glacial Erratic loop from Rockefeller State Park Preserve

8.04 km

130 m

Moderate

Buttermilk Hill USGS Benchmark – Raven's Rock loop from Pleasantville

15.6 km

310 m

Hard

Barnyard Hill Trail – Swan Lake loop from Pleasantville

20.7 km

340 m

Hard

North County Trailway loop from Pleasantville

19.0 km

70 m

Hard

Buttermilk Hill USGS Benchmark loop from Pleasantville

7.57 km

130 m

Moderate

Triple Arch Bridge – Pocantico Falls loop from Archville

7.49 km

80 m

Moderate

Brother's Path – Swan Lake loop from Rockefeller State Park Preserve

3.50 km

20 m

Easy

Graham Hills Park loop from Pleasantville

6.21 km

120 m

Hard

Running loop from Pleasantville

6.62 km

70 m

Moderate

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1.

North County Trailway loop from Briarcliff Manor

16.7km

01:44

60m

60m

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

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2.

Pocantico Falls – Glacial Erratic loop from Rockefeller State Park Preserve

8.04km

00:53

130m

130m

Embark on a delightful journey through the Rockefeller State Park Preserve with the Pocantico Falls – Glacial Erratic loop, a moderate jogging trail that offers a captivating blend of natural beauty and historical pathways. You'll traverse wide, crushed stone carriage roads, winding alongside the Pocantico River and past charming wood and stone bridges, eventually reaching the dynamic Pocantico Falls. The route's highlight is undoubtedly the massive Glacial Erratic, a 20-foot-tall, 630-ton boulder, a striking reminder of the region's ancient past, making for a truly unique experience.

This 5.0-mile (8.0 km) loop, with its 426 feet (130 metres) of elevation gain, is typically completed in about 52 minutes, making it an ideal choice for a relatively quick yet rewarding outing. The well-maintained carriage roads provide an excellent surface for jogging, and while there are some gentle inclines, the overall difficulty is moderate, suitable for a wide range of fitness levels. Parking is available at the preserve, and arriving earlier in the day is recommended, especially on weekends, to ensure a spot.

The Rockefeller State Park Preserve is renowned for its historic carriage roads, originally laid out by the Rockefeller family, which seamlessly integrate with the natural landscape. Beyond the Glacial Erratic and Pocantico Falls, the preserve is an Important Bird Area, home to over 200 bird species, offering ample opportunities for wildlife observation. This integration of history, geology, and biodiversity makes the trail a standout option for those looking to explore Westchester County's natural features.

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3.

Buttermilk Hill USGS Benchmark – Raven's Rock loop from Pleasantville

15.6km

01:44

310m

310m

The Buttermilk Hill USGS Benchmark – Raven's Rock loop from Pleasantville offers a dynamic jogging experience, transitioning from the smooth, wide historic carriage roads of the Rockefeller State Park Preserve to more rugged, natural paths. You'll wind through forested hills, past sunlit fields, and alongside streams, eventually reaching the distinctive Raven Rock with its views through the trees. This 9.6-mile (15.5 km) route, with 1006 feet (307 metres) of elevation gain, is rated difficult and takes about 1 hour and 43 minutes, making it ideal for those seeking a varied and challenging run.

Planning your visit to this loop means preparing for diverse terrain; while much of it is on well-maintained crushed stone, the sections around Buttermilk Hill and Raven Rock feature steeper descents and less manicured paths. The area around Raven Rock is known for being less crowded, offering a more remote feel. Ensure you have appropriate footwear for the varied surfaces, especially if you're tackling this trail in winter conditions.

This trail stands out for its blend of natural beauty and historical significance, traversing carriage roads originally laid out by the Rockefeller family. Buttermilk Hill, the highest point in the preserve, holds Revolutionary War lore, while Raven Rock is a massive, distinctive formation with its own legends. The varied landscape supports diverse wildlife, and you might spot hawks or other birds, adding to the natural charm of this less-trafficked part of the preserve.

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4.

Barnyard Hill Trail – Swan Lake loop from Pleasantville

20.7km

02:14

340m

340m

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

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6.

Buttermilk Hill USGS Benchmark loop from Pleasantville

7.57km

00:50

130m

130m

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

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7.

Triple Arch Bridge – Pocantico Falls loop from Archville

7.49km

00:48

80m

80m

Embark on the Triple Arch Bridge – Pocantico Falls loop from Archville for a truly scenic jogging experience through the Rockefeller State Park Preserve. This route guides you along meticulously groomed carriage roads, winding through expansive parkland, dense hardwood forests, and alongside the Pocantico River. You'll pass the historic Triple Arch Bridge, a notable landmark, and witness the dynamic beauty of Pocantico Falls, the largest waterfall in the preserve, which changes dramatically with the seasons.

This moderate 4.7-mile (7.5 km) loop, with 266 feet (81 metres) of elevation gain, can be completed in approximately 47 minutes, making it a perfect option for a quick, invigorating run. The wide, crushed stone paths are suitable for all skill levels, though you'll encounter some rolling hills. Parking is generally available in the Archville area, but arriving earlier in the day is advisable, especially on weekends, to secure a spot and enjoy the trails before they get busy.

The preserve is renowned for its historic carriage roads, built by the Rockefeller family, and its ecological significance as an Important Bird Area, hosting over 200 bird species. These natural features, combined with the architectural marvel of the Triple Arch Bridge and the natural spectacle of Pocantico Falls, make this loop a standout among popular trails in Westchester County, New York.

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9.

Graham Hills Park loop from Pleasantville

6.21km

00:48

120m

120m

The Graham Hills Park loop from Pleasantville offers a demanding yet deeply satisfying jogging experience, winding through a surprisingly secluded mature hardwood forest. You'll encounter a mix of singletrack and doubletrack, with plenty of exposed stone and rooty sections underfoot, providing a true technical challenge. The varied terrain and "punchy elevation changes" ensure a dynamic workout, making it a favorite among local trail runners.

This difficult 3.9-mile (6.2 km) route, with its 395 feet (121 metres) of elevation gain, can be completed in about 48 minutes, making it an excellent option for a focused, high-intensity run. The park is easily accessible via public transport; take the Metro-North to Pleasantville station, followed by a short one-mile walk to the trailhead. Parking is available, but it's always wise to arrive early on busy days.

Graham Hills Park is renowned for its tightly woven and interconnected trail network, allowing for numerous loop combinations beyond this specific route. It's a popular spot for outdoor enthusiasts, including mountain bikers and hikers, all sharing the diverse habitats and quiet woodland experience. The park's accessibility and challenging terrain make it a standout choice for those seeking best jogging routes near Pleasantville NY.

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Tips from the Community

Hans
June 5, 2025, South County Trail (Elmsford to Tarrytown Lakes)

Great trail and only occasional crossing traffic

Translated by Google

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This is a beautiful section of the North County Trail that runs between Elmsford to Tarrytown Lakes. At the north end of this section, the trail intersects with Tarrytown Lakes Extension Trail, a paved path with takes you along the banks of Tarrytown Reservoir.

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Great section of the North County Trailway. The paved path passes through a beautiful wooded area. As the trail gets to Tarrytown Reservior, there is an area with benches for a break.

0

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Beautiful little lake at the park entrance

Translated by Google

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The area is very beautiful.

Translated by Google

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This is a really nice spot to sit, relax and take in the wildlife.

1

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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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Frequently Asked Questions

How many running routes are available in Pleasantville?

Pleasantville offers a wide selection of jogging routes, with over 50 different tours available for exploration. These routes cater to various fitness levels, ranging from easy paths to more challenging trails.

What kind of terrain can I expect on jogging routes in Pleasantville?

Jogging routes in Pleasantville feature diverse landscapes, including extensive woodlands, rolling meadows, and river valleys. You'll find well-maintained crushed stone carriage roads, particularly within the Rockefeller State Park Preserve, alongside paths that follow historic aqueducts. The terrain varies from gentle, relatively flat sections to trails with moderate elevation changes.

Are there any easy running trails suitable for beginners in Pleasantville?

Yes, Pleasantville has several easy running trails perfect for beginners. For instance, the Barnyard Hill Trail – Swan Lake loop from Rockefeller State Park Preserve is a moderate route that winds through woodlands and past Swan Lake, offering a pleasant experience. The Rockefeller State Park Preserve generally offers many gentle paths suitable for those new to running.

Can I bring my dog on the running trails in Pleasantville?

Many trails in Pleasantville, especially within the Rockefeller State Park Preserve, are dog-friendly. It's always a good idea to check specific park regulations or trail signs for any restrictions, but generally, leashed dogs are welcome to join you on your run.

Are there family-friendly jogging options in Pleasantville?

Absolutely. The Rockefeller State Park Preserve, with its extensive network of crushed stone carriage roads, is an excellent choice for families. Shorter loops like the Swan Lake Loop (approximately 2.5 miles) offer an accessible and enjoyable experience for all ages. Local parks such as Nannahagan Park also provide green spaces for more casual outdoor activities.

What natural features or landmarks can I see while jogging in Pleasantville?

While jogging in Pleasantville, you can encounter beautiful natural features like Swan Lake and the Pocantico River, especially within the Rockefeller State Park Preserve. Historic paths such as the Old Croton Aqueduct State Historic Trail offer views of the Hudson River. Other notable highlights in the broader area include the Kensico Reservoir and the Tarrytown Reservoir.

Are there circular running routes available?

Yes, many of the jogging routes in Pleasantville are designed as loops, offering a convenient circular experience. Examples include the popular Barnyard Hill Trail – Swan Lake loop from Rockefeller State Park Preserve and the Buttermilk Hill USGS Benchmark loop from Village of Pleasantville.

What are the parking options for accessing jogging trails, especially in Rockefeller State Park Preserve?

The Rockefeller State Park Preserve, a prime destination for joggers, offers dedicated parking facilities for visitors. Additionally, many trailheads throughout Pleasantville provide convenient parking access. It's advisable to check specific route details for the most accurate parking information.

Is public transport available to reach the running routes?

Pleasantville is accessible by public transport, which can help you reach various parts of the village and access points for trails. For specific routes, especially those within the Rockefeller State Park Preserve, checking local bus schedules or regional train lines (like the Metro-North Harlem Line to Pleasantville station) is recommended to plan your journey.

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

Pleasantville offers excellent jogging opportunities year-round. Spring and fall provide pleasant temperatures and beautiful foliage. Summer is great for early morning or late afternoon runs, while winter transforms the Rockefeller State Park Preserve into a scenic location for cross-country skiing and snowshoeing, which can also be enjoyed by runners seeking a different experience.

What do other runners say about the trails in Pleasantville?

The jogging routes in Pleasantville are highly rated by the komoot community, with an average score of 5.0 stars. Runners often praise the diverse terrain, well-maintained paths, and the scenic beauty of areas like the Rockefeller State Park Preserve, highlighting the peaceful woodlands and picturesque fields.

Are there any specific trails known for scenic viewpoints?

Yes, many trails in Pleasantville offer scenic viewpoints, particularly those within the Rockefeller State Park Preserve which wind through rolling meadows and valleys. The Old Croton Aqueduct State Historic Trail also provides scenic views, including glimpses of the Hudson River. For a route with varied landscapes and open sections, consider the Buttermilk Hill USGS Benchmark loop from Village of Pleasantville.

Can I find jogging routes that follow historic paths?

Absolutely. The Old Croton Aqueduct State Historic Trail is a prime example, following the path of the 19th-century aqueduct that once supplied water to New York City. This trail offers a unique blend of history and natural beauty for your run.

Are there any longer running routes for experienced runners?

Experienced runners will find several longer and more challenging routes. For instance, the North County Trailway loop from Village of Pleasantville is an 11.6-mile (18.7 km) trail leading through varied landscapes. The North County Trailway loop from Village of Briarcliff Manor is another difficult option, spanning over 10 miles.

Are there any amenities like cafes near the jogging routes?

Pleasantville village itself is known for its friendly atmosphere and offers various local amenities, including cafes and shops. After your run, you can easily find places to refuel and relax within the village, especially if your route starts or ends near the village center.

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