RoutesPlannerFeaturesUpdates
App
Login or Signup
Get the App
Login or Signup
Routes
Running Trails
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 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

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

Sign up to see all 10 routes

Sign up for free

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.

View route

Save
Navigate with deviceSend to Phone
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.
Sign up for free

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.

View route

5.

North County Trailway loop from Pleasantville

19.0km

01:58

70m

70m

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

View route

Sign up for free to see 5 more runs around Pleasantville.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

See every route on the map

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•

0

0

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.

1

0

Beautiful little lake at the park entrance

Translated by Google•

1

0

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

1

0

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.

0

0

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.

0

0

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.

1

0

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.

0

0

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.

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now
Store rating

Explore more

Browse the best Running Trails & Routes in other regions.

VerplanckOssiningMontrosePeekskillVillage of BuchananMontrose Point State ForestCrugersCroton-On-HudsonYonkersPelham ManorHawthorneThornwoodSleepy HollowNew RochelleVillage of TarrytownMamaroneckEastchesterTuckahoeMount VernonBriarcliff ManorRockefeller State Park PreserveValhallaPelhamElmsfordBronxvilleMillwoodGreenvilleTown/Village of HarrisonBedford HillsArmonkRyeKatonahScotts CornersBedfordWhite PlainsArdsleyRye BrookMount KiscoLarchmontGolden'S BridgePort ChesterShrub OakVillage of Hastings-on-HudsonVillage of IrvingtonScarsdaleChappaquaHartsdaleJefferson Valley-YorktownVillage of Dobbs FerryFairviewShenorockYorktown HeightsSalt Hill State ForestHeritage HillsLincolndaleDonald J. Trump State Park (French Hill Unit) (Closed)Franklin Delano Roosevelt State ParkCrompondLake Mohegan
background

Get ready to conquer new peaks

Sign up for Free
Explore
RoutesRoute plannerFeaturesRedeem a voucherHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy