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Westchester County

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144 mi 231 km of trail 14 Featured Runs

Easy Trails 57 Trails Intermediate Trails 44 Trails Hard Trails 2 Trails
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Featured Runs in Westchester County - 14

Trail Run Project is built by runners like you. Add Your Runs

Favorite Raven Rocks overlook panorama.
Intermediate/Difficult

Rock Trail (RT) Loop

7.0 mi 11.3 km • Loop • 1,035 ft Ascent 315.48 m Ascent

(12) Pound R…, NY
Favorite View from Anthony's Nose,  across the Hudson looking at Bear Mountain.
Intermediate/Difficult

Anthony's Nose to Bear Mountain Bridge

6.0 mi 9.6 km • Out and Back • 1,446 ft Ascent 440.79 m Ascent

(5) Fort Mo…, NY
Favorite Runners approach the Gazebo hill about 1/2 mile into Run The Farm 2014.
Intermediate/Difficult

Run The Farm 5 Mile Trail Race

5.1 mi 8.2 km • Loop • 591 ft Ascent 180.21 m Ascent

(1) Katonah, NY
Favorite View from Anthony's Nose,  across the Hudson looking at Bear Mountain.
Intermediate

Manitou to Camp Smith Trail

6.3 mi 10.1 km • Point to Point • 1,650 ft Ascent 502.91 m Ascent

(1) Fort Mo…, NY
Favorite On the Cole Kettle boardwalk
Intermediate

Westmoreland Sanctuary

5.4 mi 8.7 km • Loop • 717 ft Ascent 218.65 m Ascent

(2) Bedford, NY
Favorite Raven Rocks overlook panorama.
Intermediate/Difficult

Raven Rocks Run 10k

6.5 mi 10.5 km • Point to Point • 892 ft Ascent 271.85 m Ascent

(2) Katonah, NY

Trails in Westchester County - 89

Trail Run Project is built by runners like you. Add Your Trails

1.2 mi 1.9 km #1Leatherman's Loop Overlook
Intermediate
Pound Ridge, NY
Intermediate
1.2 mi 1.9 km Pound Ridge, NY
0.5 mi 0.8 km #2Meyer Aqueduct Trail
Easy/Intermediate
Armonk, NY
Easy/Intermediate
0.5 mi 0.8 km Armonk, NY
1.0 mi 1.6 km #3Green Trail
Easy/Intermediate
Goldens Bridge, NY
Easy/Intermediate
1.0 mi 1.6 km Goldens Bridge, NY
1.3 mi 2.0 km #4Blue Trail
Intermediate/Difficult
Mount Kisco, NY
Intermediate/Difficult
1.3 mi 2.0 km Mount Kisco, NY
1.0 mi 1.7 km #5Blue Trail
Intermediate/Difficult
Armonk, NY
Intermediate/Difficult
1.0 mi 1.7 km Armonk, NY
0.5 mi 0.8 km #6Lower Orange Trail
Intermediate
Armonk, NY
Intermediate
0.5 mi 0.8 km Armonk, NY
0.4 mi 0.6 km #7Law Memorial Park Walking Path
Easy
Briarcliff Manor, NY
Easy
0.4 mi 0.6 km Briarcliff Manor, NY
2.5 mi 4.1 km #8Fox Hill
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
2.5 mi 4.1 km Pound Ridge, NY
5.3 mi 8.6 km #9Rock Trail
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
5.3 mi 8.6 km Pound Ridge, NY
2.1 mi 3.3 km #1013 Bridges Trail
Easy
Sleepy Hollow, NY
Easy
2.1 mi 3.3 km Sleepy Hollow, NY
2.7 mi 4.4 km #11Zofnass Southern Loop
Intermediate
Pound Ridge, NY
Intermediate
2.7 mi 4.4 km Pound Ridge, NY
5.7 mi 9.2 km #12Red Trail
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
5.7 mi 9.2 km Pound Ridge, NY
4.0 mi 6.5 km #13Deer Hollow
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
4.0 mi 6.5 km Pound Ridge, NY
3.2 mi 5.2 km #14Green Trail
Easy/Intermediate
Pound Ridge, NY
Easy/Intermediate
3.2 mi 5.2 km Pound Ridge, NY
3.5 mi 5.6 km #15Camp Smith Trail
Intermediate/Difficult
Peekskill, NY
Intermediate/Difficult
3.5 mi 5.6 km Peekskill, NY
3.9 mi 6.3 km #16Blue Trail
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
3.9 mi 6.3 km Pound Ridge, NY
1.1 mi 1.8 km #17Brothers' Path
Easy
Hawthorne, NY
Easy
1.1 mi 1.8 km Hawthorne, NY
3.4 mi 5.5 km #18Brown Trail
Intermediate
Pound Ridge, NY
Intermediate
3.4 mi 5.5 km Pound Ridge, NY
1.6 mi 2.6 km #19Yellow Trail
Intermediate
Mount Kisco, NY
Intermediate
1.6 mi 2.6 km Mount Kisco, NY
1.3 mi 2.1 km #20Red Trail
Easy/Intermediate
Mount Kisco, NY
Easy/Intermediate
1.3 mi 2.1 km Mount Kisco, NY

Photos of Westchester County - 70

Trail Run Project is built by runners like you. Add Your Photos

Croton Dam spillway from Croton Point Park
Feb 1, 2019 near Croton-…, NY
View from Anthony's Nose,  across the Hudson looking at Bear Mountain.
Oct 5, 2018 near Fort Mo…, NY
Raven Rocks overlook panorama.
Dec 21, 2015 near Pound R…, NY
Heading out from the trailhead on a group run
Jun 18, 2015 near Mount K…, NY
Snowy run on the Red Trail.
Dec 21, 2015 near Pound R…, NY
View of the Michigan Road campground meadow and hills.
Dec 21, 2015 near Pound R…, NY
Runners crossing Michigan Road campground area.
Dec 21, 2015 near Pound R…, NY
Runners heading uphill from the new Covered Bridge.
Dec 21, 2015 near Pound R…, NY

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