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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 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
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Sleepy Hollow Hiking

  • 38 Miles 62 Kilometers of Trail
  • 1 Recommended Route
  • 36 Easy Trails Easy Trails
  • 3 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 - 38

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14.6 mi 23.5 km #1South County Trail
Easy Easy
Tarrytown, NY
Easy Easy
Tarrytown, NY
2.1 mi 3.3 km #213 Bridges Trail
Easy Easy
Sleepy Hollow, NY
Easy Easy
Sleepy Hollow, NY
1.1 mi 1.8 km #3Brothers' Path
Easy Easy
Hawthorne, NY
Easy Easy
Hawthorne, NY
1.0 mi 1.6 km #4Ridge Trail
Easy Easy
Hawthorne, NY
Easy Easy
Hawthorne, NY
0.8 mi 1.2 km #5Brook Trail
Easy Easy
Hawthorne, NY
Easy Easy
Hawthorne, NY
0.6 mi 1.0 km #6Foundation Loop
Easy Easy
Sleepy Hollow, NY
Easy Easy
Sleepy Hollow, NY
0.7 mi 1.2 km #7Old Sleepy Hollow Road Trail
Easy/Intermediate Easy/Intermediate
Hawthorne, NY
Easy/Intermediate Easy/Intermediate
Hawthorne, NY
1.8 mi 2.9 km #8Lucy's Loop
Easy/Intermediate Easy/Intermediate
Pleasantville, NY
Easy/Intermediate Easy/Intermediate
Pleasantville, NY
1.8 mi 2.9 km #9Pocantico River Trail
Easy Easy
Sleepy Hollow, NY
Easy Easy
Sleepy Hollow, NY
0.5 mi 0.9 km #10Witch's Spring Trail
Easy Easy
Sleepy Hollow, NY
Easy Easy
Sleepy Hollow, NY

Photos of Sleepy Hollow - 3

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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
Crossing the Pocantico River in early spring
Apr 2, 2018 near Sleepy…, NY
Small dog, very large glacial erratic.
Apr 2, 2018 near Sleepy…, NY

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