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Westchester County

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148 mi 238 km of trail 14 Recommended Routes

Easy Trails 40 Trails Intermediate Trails 56 Trails Hard Trails 10 Trails
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Recommended Routes in Westchester County - 14

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Favorite Raven Rocks overlook panorama.
Difficult

Rock Trail (RT) Loop

7.0 mi 11.3 km 1,035' Up 315.48 m Up 1,034' Down 315.22 m Down

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 1,446' Up 440.79 m Up 1,446' Down 440.69 m Down

Fort Mo…, 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 1,650' Up 502.91 m Up 1,471' Down 448.48 m Down

Fort Mo…, NY
Favorite No Photos
Intermediate

Leatherman's Loop

6.4 mi 10.3 km 505' Up 153.9 m Up 505' Down 153.96 m Down

Katonah, NY
Favorite Runners approach the Gazebo hill about 1/2 mile into Run The Farm 2014.
Difficult

Run The Farm 5 Mile Trail Race

5.1 mi 8.2 km 591' Up 180.21 m Up 593' Down 180.61 m Down

Katonah, NY
Favorite Pocantico Park Trailhead on Laurel Lane
Intermediate/Difficult

Pocantico Park Loop

0.9 mi 1.5 km 180' Up 54.73 m Up 180' Down 54.73 m Down

Briarcl…, NY
Favorite No Photos
Easy

Old Croton Aqueduct - Dam to Briarcliff

15.0 mi 24.1 km 342' Up 104.12 m Up 342' Down 104.13 m Down

Croton-…, NY
Favorite Raven Rocks overlook panorama.
Difficult

Raven Rocks Run 10k

6.5 mi 10.5 km 892' Up 271.85 m Up 899' Down 274.14 m Down

Katonah, NY

Trails in Westchester County - 92

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

1.9 mi 3.1 km #1North County Trailway: Law Park South to Route 117
Intermediate
Briarcliff Manor, NY
Intermediate
Briarcliff Manor, NY
0.4 mi 0.6 km #2Law Memorial Park Walking Path
Easy
Briarcliff Manor, NY
Easy
Briarcliff Manor, NY
0.5 mi 0.8 km #3Meyer Aqueduct Trail
Intermediate
Armonk, NY
Intermediate
Armonk, NY
1.0 mi 1.6 km #4Green Trail
Intermediate
Goldens Bridge, NY
Intermediate
Goldens Bridge, NY
0.3 mi 0.5 km #5Richard Wishnie Park Walking Path
Easy
Ossining, NY
Easy
Ossining, NY
1.3 mi 2.0 km #6Blue Trail
Difficult
Mount Kisco, NY
Difficult
Mount Kisco, NY
1.0 mi 1.7 km #7Blue Trail
Difficult
Armonk, NY
Difficult
Armonk, NY
0.5 mi 0.8 km #8Lower Orange Trail
Intermediate
Armonk, NY
Intermediate
Armonk, NY
2.5 mi 4.1 km #9Fox Hill
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
Pound Ridge, NY
2.1 mi 3.3 km #1013 Bridges Trail
Easy
Sleepy Hollow, NY
Easy
Sleepy Hollow, NY
5.3 mi 8.6 km #11Rock Trail
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
Pound Ridge, NY
5.7 mi 9.2 km #12Red Trail
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
Pound Ridge, NY
3.2 mi 5.2 km #13Green Trail
Intermediate
Pound Ridge, NY
Intermediate
Pound Ridge, NY
4.0 mi 6.5 km #14Deer Hollow
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
Pound Ridge, NY
2.7 mi 4.4 km #15Zofnass Southern Loop
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
Pound Ridge, NY
3.5 mi 5.6 km #16Camp Smith Trail
Difficult
Peekskill, NY
Difficult
Peekskill, NY
3.9 mi 6.3 km #17Blue Trail
Intermediate/Difficult
Pound Ridge, NY
Intermediate/Difficult
Pound Ridge, NY
1.2 mi 1.9 km #18Kazimiroff Nature Trail
Intermediate
Pelham Manor, NY
Intermediate
Pelham Manor, NY
1.2 mi 1.9 km #19Leatherman's Loop Overlook
Intermediate
Pound Ridge, NY
Intermediate
Pound Ridge, NY
1.1 mi 1.8 km #20Brothers' Path
Easy
Hawthorne, NY
Easy
Hawthorne, NY

Photos of Westchester County - 80

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