5.0
(3)
205
runners
31
runs
Jogging around Chappaqua, located in Westchester County, offers routes through a landscape characterized by hilly terrain and lush greenery. The region features rolling hills, hardwood forests, and centuries-old stone walls, providing a natural setting for outdoor activities. Numerous parks, trails, and nature preserves contribute to the area's appeal for runners. The varied topography includes accessible paths and more challenging routes with elevation changes.
Last updated: April 29, 2026
17
runners
16.7km
01:43
60m
60m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
15
runners
20.7km
02:14
340m
340m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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11
runners
15.6km
01:44
310m
310m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
runners
19.0km
01:58
70m
70m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
runners
7.54km
00:49
130m
130m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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 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 really nice spot to sit, relax and take in the wildlife.
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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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The Chappaqua area offers a wide variety of running routes, with over 30 options available on komoot. These routes cater to different preferences, ranging from easy paths to more challenging trails.
Runners in Chappaqua can expect a diverse landscape characterized by hilly terrain and lush greenery. Many routes feature rolling hills, hardwood forests, and centuries-old stone walls. You'll find a mix of paved surfaces, especially on popular trails like the North County Trailway, and natural paths within parks and preserves.
Yes, Chappaqua offers several easy running options. For instance, the Glazier Arboretum provides a range of very easy and easy trails. Overall, komoot lists 5 easy routes in the area, perfect for a gentle run or a peaceful nature walk.
Absolutely. For those seeking a more strenuous workout, Chappaqua has 5 difficult running routes. A notable challenging option is the North County Trailway loop from Village of Briarcliff Manor, which spans 10.4 miles (16.7 km) and includes elevation changes, making it a great choice for experienced runners.
Many of the running routes in Chappaqua are designed as loops, offering a convenient way to start and finish in the same location. Popular examples include the Barnyard Hill Trail – Swan Lake loop from Rockefeller State Park Preserve and the Buttermilk Hill USGS Benchmark loop from Village of Pleasantville.
Chappaqua's running routes are rich with natural beauty. You can encounter serene ponds, hardwood forests, and historic stone walls. Nearby attractions include the scenic Kensico Reservoir, known for its views, and the impressive Pocantico Falls, which transforms with the seasons.
Given the region's rolling hills and lush landscapes, many routes offer picturesque views. The Kensico Reservoir, accessible from some trails, provides expansive scenic vistas. The elevated sections of trails like the Buttermilk Hill USGS Benchmark loop from Hawthorne can also provide rewarding outlooks over the surrounding countryside.
Yes, Chappaqua is a great place for running with your canine companion. The Glazier Arboretum, for example, offers trails that are suitable for people of all ages and dogs. Always check specific park regulations, but many natural areas in Chappaqua welcome leashed dogs.
Many of the easier trails in Chappaqua are suitable for families. The Glazier Arboretum is specifically noted for its very easy and easy trails, making it a good option for families with children. Parks like Gedney Park also offer peaceful nature walks that can be enjoyed by all ages.
The running routes in Chappaqua are highly rated by the komoot community, with an average score of 5.0 stars from 3 reviews. Runners often praise the area's natural beauty, including its quiet woodlands, rolling hills, and well-maintained paths, providing a serene escape from urban life.
While specific public transport connections to every trailhead may vary, Chappaqua is located in Westchester County, which has public transportation options. It's advisable to check local bus schedules or train services to nearby villages like Pleasantville or Briarcliff Manor, which are starting points for popular trails like the North County Trailway.
Many of the popular parks and trailheads in and around Chappaqua, such as Rockefeller State Park Preserve and Gedney Park, offer designated parking areas for visitors. When planning your run, it's always a good idea to check the specific starting point of your chosen route for parking availability.
Chappaqua's natural beauty makes it appealing year-round. Spring and fall offer pleasant temperatures and vibrant scenery with lush greenery or colorful foliage. Summer can be warm, so early morning or late evening runs are often preferred. Winter running is also possible, with trails transforming into a peaceful, snow-covered landscape, though conditions may require appropriate gear.


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