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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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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.
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 | 7.97 km | 130 m | Moderate |
| Buttermilk Hill USGS Benchmark loop from Pleasantville | 14.1 km | 260 m | Moderate |
| 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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Sign up for free16.7km
01:44
60m
60m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
7.97km
00:52
130m
130m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
14.1km
01:33
260m
260m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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20.7km
02:14
340m
340m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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19.0km
01:58
70m
70m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
7.57km
00:50
130m
130m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
7.49km
00:48
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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3.50km
00:22
20m
20m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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6.21km
00:48
120m
120m
Hard run. Good fitness required. Sure-footedness, sturdy shoes and alpine experience required.
View route
6.62km
00:42
70m
70m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
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Great trail and only occasional crossing traffic
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Beautiful little lake at the park entrance
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This is a really nice spot to sit, relax and take in the wildlife.
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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 part of Barnyard Hill provides lots of shade, which definitely makes for a more pleasant hike in those hot summer months. It also makes for a very beautiful hike in the fall when the leaves start to change colors.
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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 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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