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Sleepy Hollow

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Recommended Routes 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 139' Up 42.4 m Up 139' Down 42.33 m Down

Sleepy…, NY

Sleepy Hollow Hiking

  • 45 Miles 72 Kilometers of Trail
  • 1 Recommended Route
  • 33 Easy Trails Easy Trails
  • 0 Intermediate Trails Intermediate Trails
  • 0 Difficult Trails Difficult Trails
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Areas Within Sleepy Hollow

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Trails in Sleepy Hollow - 32

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14.6 mi 23.5 km #1South County Trail
Easy
Tarrytown, NY
Easy
Tarrytown, NY
3.6 mi 5.8 km #2North-South County Trailway: New Castle Section: Route 117 to…
Easy
Pleasantville, NY
Easy
Pleasantville, NY
2.1 mi 3.3 km #313 Bridges Trail
Easy
Sleepy Hollow, NY
Easy
Sleepy Hollow, NY
1.1 mi 1.8 km #4Brothers' Path
Easy
Hawthorne, NY
Easy
Hawthorne, NY
1.0 mi 1.6 km #5Ridge Trail
Easy
Hawthorne, NY
Easy
Hawthorne, NY
4.7 mi 7.6 km #6Governor Mario M. Cuomo Bridge
Easy/Intermediate
South Nyack, NY
Easy/Intermediate
South Nyack, NY
0.8 mi 1.2 km #7Brook Trail
Easy
Hawthorne, NY
Easy
Hawthorne, NY
0.6 mi 1.0 km #8Foundation Loop
Easy
Sleepy Hollow, NY
Easy
Sleepy Hollow, NY
0.7 mi 1.2 km #9Old Sleepy Hollow Road Trail
Easy/Intermediate
Hawthorne, NY
Easy/Intermediate
Hawthorne, NY
1.8 mi 2.9 km #10Pocantico River Trail
Easy
Sleepy Hollow, NY
Easy
Sleepy Hollow, NY

Photos of Sleepy Hollow - 3

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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