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Sleepy Hollow

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20 mi 33 km of trail 1 Featured Run

Easy Trails 30 Trails Intermediate Trails 0 Trails Hard Trails 0 Trails
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Featured Runs in Sleepy Hollow - 1

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Favorite Even when it's a bit hazy on hot humid days, you can still enjoy nice views of the Hudson from the Lower Trail.
Easy

Rockwood Hall Short Loop

1.3 mi 2.2 km • Loop • 139 ft Ascent 42.4 m Ascent

(1) Sleepy…, NY

Trails in Sleepy Hollow - 29

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2.1 mi 3.3 km #113 Bridges Trail
Easy
Sleepy Hollow, NY
Easy
2.1 mi 3.3 km Sleepy Hollow, NY
1.1 mi 1.8 km #2Brothers' Path
Easy
Hawthorne, NY
Easy
1.1 mi 1.8 km Hawthorne, NY
0.8 mi 1.2 km #3Brook Trail
Easy
Hawthorne, NY
Easy
0.8 mi 1.2 km Hawthorne, NY
0.6 mi 1.0 km #4Foundation Loop
Easy
Sleepy Hollow, NY
Easy
0.6 mi 1.0 km Sleepy Hollow, NY
1.8 mi 2.9 km #5Pocantico River Trail
Easy
Sleepy Hollow, NY
Easy
1.8 mi 2.9 km Sleepy Hollow, NY
0.9 mi 1.4 km #6Eagle Hill Trail
Easy
Sleepy Hollow, NY
Easy
0.9 mi 1.4 km Sleepy Hollow, NY
0.7 mi 1.2 km #7Old Sleepy Hollow Road Trail
Easy
Hawthorne, NY
Easy
0.7 mi 1.2 km Hawthorne, NY
0.2 mi 0.3 km #8Spook Rock Trail
Easy
Sleepy Hollow, NY
Easy
0.2 mi 0.3 km Sleepy Hollow, NY
0.7 mi 1.1 km #9Overlook Trail
Easy
Hawthorne, NY
Easy
0.7 mi 1.1 km Hawthorne, NY
0.9 mi 1.4 km #10Big Tree Loop
Easy
Sleepy Hollow, NY
Easy
0.9 mi 1.4 km Sleepy Hollow, NY
0.5 mi 0.9 km #11Witch's Spring Trail
Easy
Sleepy Hollow, NY
Easy
0.5 mi 0.9 km Sleepy Hollow, NY
1.0 mi 1.6 km #12Ridge Trail
Easy
Hawthorne, NY
Easy
1.0 mi 1.6 km Hawthorne, NY
0.4 mi 0.7 km #13Nature's Way
Easy
Hawthorne, NY
Easy
0.4 mi 0.7 km Hawthorne, NY
0.3 mi 0.5 km #14Rockwood Hall Brook Trail
Easy
Sleepy Hollow, NY
Easy
0.3 mi 0.5 km Sleepy Hollow, NY
1.0 mi 1.5 km #15David's Loop
Easy
Hawthorne, NY
Easy
1.0 mi 1.5 km Hawthorne, NY
0.8 mi 1.2 km #16Ash Tree Loop
Easy
Sleepy Hollow, NY
Easy
0.8 mi 1.2 km Sleepy Hollow, NY
0.4 mi 0.6 km #17Deer Run
Easy
Hawthorne, NY
Easy
0.4 mi 0.6 km Hawthorne, NY
0.9 mi 1.5 km #18Lower Trail
Easy
Sleepy Hollow, NY
Easy
0.9 mi 1.5 km Sleepy Hollow, NY
0.4 mi 0.7 km #19Farm Meadow Trail
Easy
Hawthorne, NY
Easy
0.4 mi 0.7 km Hawthorne, NY
0.5 mi 0.7 km #20Raven's Rock Trail
Easy
Hawthorne, NY
Easy
0.5 mi 0.7 km Hawthorne, NY
1.0 mi 1.6 km #21Goat Trail
Easy
Hawthorne, NY
Easy
1.0 mi 1.6 km Hawthorne, NY
0.4 mi 0.6 km #22Gory Brook Road Trail
Easy
Sleepy Hollow, NY
Easy
0.4 mi 0.6 km Sleepy Hollow, NY
0.8 mi 1.2 km #23Laurance's Ridge Trail
Easy
Hawthorne, NY
Easy
0.8 mi 1.2 km Hawthorne, NY
0.5 mi 0.8 km #24Upper Trail
Easy
Sleepy Hollow, NY
Easy
0.5 mi 0.8 km Sleepy Hollow, NY
0.2 mi 0.4 km #25OCA Connector
Easy
Sleepy Hollow, NY
Easy
0.2 mi 0.4 km Sleepy Hollow, NY
0.6 mi 0.9 km #26Peggy's Way Trail
Easy
Sleepy Hollow, NY
Easy
0.6 mi 0.9 km Sleepy Hollow, NY
0.4 mi 0.6 km #27Old Railroad Bed
Easy
Hawthorne, NY
Easy
0.4 mi 0.6 km Hawthorne, NY
0.3 mi 0.5 km #28Peaceful Path
Easy
Hawthorne, NY
Easy
0.3 mi 0.5 km Hawthorne, NY
0.2 mi 0.4 km #29Middle Trail
Easy
Sleepy Hollow, NY
Easy
0.2 mi 0.4 km Sleepy Hollow, NY

Photos of Sleepy Hollow - 3

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

Small dog, very large glacial erratic.
Apr 2, 2018 near Sleepy…, NY
Crossing the Pocantico River in early spring
Apr 2, 2018 near Sleepy…, NY
Even when it's a bit hazy on hot humid days, you can still enjoy nice views of the Hudson from the Lower Trail.
Apr 2, 2017 near Sleepy…, NY

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