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Trails near Ossining, NY

1,313 trails within 30 miles of Ossining, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (1,283) Walking trails (1,253) Bike trails (386) Mountain bike trails (235) Paved trails (220) Horse trails (157) ATV and UTV trails (3) Off-road and 4x4 trails (5) Dog-friendly trails (19) Snowmobile trails (19) Cross-country ski trails (5) Wheelchair-accessible trails (10) Rail trails (12) Greenways (40)

Quick picks

All nearby trails

Old Croton Aqueduct Trail

0.1 mi away

1.7 mi long · Hard · Ossining

Hiking Biking Mountain biking

Hudson Loop

0.6 mi away

0.7 mi long · Easy · Ossining

Hiking

Briarcliff-Peekskill Trailway

1.3 mi away

12 mi long · Easy · Westchester County Parks

Hiking Paved

Old Croton Aqueduct Trail

1.6 mi away

3.1 mi long · Easy · Croton-on-Hudson

Hiking Biking Mountain biking

Old Croton Aqueduct Trail

1.7 mi away

1.1 mi long · Ossining

Hiking Biking Mountain biking

White Trail

2.2 mi away

0.8 mi long · Ossining

Hiking

Kate Kennard Trail

2.3 mi away

0.9 mi long · Easy · Briarcliff Manor

Hiking Biking Paved

Red Trail

3.0 mi away

0.7 mi long · Briarcliff Manor

Hiking

Yellow Trail

3.0 mi away

0.4 mi long · Briarcliff Manor

Hiking

Red Trail

3.0 mi away

0.7 mi long · Briarcliff Manor

Hiking Biking Mountain biking

Catamount Hill Loop

3.0 mi away

1.0 mi long · Teatown Lake Reservation

Hiking

Blue Trail

3.0 mi away

0.4 mi long · Briarcliff Manor

Hiking

Croton RiverWalk

3.1 mi away

1.3 mi long · Easy · Croton-on-Hudson

Hiking Biking Paved Wheelchair accessible

Croton Gorge Trail

3.1 mi away

0.6 mi long · Croton on Hudson Trails Committee

Hiking Biking Mountain biking

White Trail

3.1 mi away

1.3 mi long · Briarcliff Manor

Hiking Biking Mountain biking

Rockland Lake Jogging and Bike Path

3.2 mi away

3.0 mi long · No dogs · Congers

Hiking Biking Mountain biking

Cliffdale Loop

3.3 mi away

1.7 mi long · Teatown Lake Reservation

Hiking

Cliffdale-Teatown Trail

3.3 mi away

0.8 mi long · Teatown Lake Reservation

Hiking

Hudson Valley Greenway Trail (New Castle to Mahopac)

3.3 mi away

16 mi long · Easy · Empire State Trails

Hiking Biking Paved Greenway

Lakeside Loop

3.4 mi away

1.6 mi long · Teatown Lake Reservation

Hiking

Upper Village Trail Loop

3.5 mi away

1.6 mi long · Croton on Hudson Trails Committee

Hiking

Foundation Loop

3.5 mi away

0.6 mi long · Easy · Sleepy Hollow

Hiking Horses Paved

Lower Loop

3.6 mi away

0.9 mi long · Sleepy Hollow

Hiking Horses

Yellow Trail

3.6 mi away

0.6 mi long · Chappaqua

Hiking

Red Trail

3.7 mi away

1.1 mi long · Chappaqua

Hiking

Doc's Trail

3.7 mi away

0.9 mi long · Briarcliff Manor

Hiking Horses

Vernay Lakeside Connector

3.7 mi away

0.4 mi long · Ossining

Hiking

Phenology Trail

3.7 mi away

0.4 mi long · Ossining

Hiking

Old Sleepy Hollow Road Trail

3.8 mi away

0.7 mi long · Sleepy Hollow

Hiking Horses

Three Lakes Loop

3.8 mi away

3.5 mi long · Teatown Lake Reservation

Hiking

Boulders Loop

3.8 mi away

2.8 mi long · Upper Nyack

Hiking

Nyack River Trail

3.8 mi away

1.3 mi long · Easy · Upper Nyack

Hiking Biking Paved

13 Bridges Loop

3.8 mi away

2.0 mi long · Sleepy Hollow

Hiking Horses

Brothers' Path

3.8 mi away

1.1 mi long · Sleepy Hollow

Hiking Horses

Blue Trail

3.8 mi away

0.4 mi long · Chappaqua

Hiking

Purple Trail

3.9 mi away

0.3 mi long · Chappaqua

Hiking

Brook Trail

3.9 mi away

0.8 mi long · Hawthorne

Hiking Horses

Witch's Spring Trail

4.0 mi away

0.6 mi long · Sleepy Hollow

Hiking Horses

Hidden Valley Loop

4.0 mi away

1.4 mi long · Teatown Lake Reservation

Hiking

David's Loop

4.0 mi away

0.9 mi long · Hawthorne

Hiking Horses

Pink Trail

4.0 mi away

1.8 mi long · Easy · Hawthorne

Hiking Biking Mountain biking

Teatown-Kitchawan Trail

4.0 mi away

6.5 mi long · No dogs · Teatown Lake Reservation, New York City Department of Environmental Protection, Westchester County Parks Deparment

Hiking

Eagle Hill

4.0 mi away

0.9 mi long · Sleepy Hollow

Hiking Horses

Blue Trail

4.0 mi away

1.2 mi long · Chappaqua

Hiking

Kaplan's Pond Trail

4.0 mi away

0.2 mi long · Easy · Croton on Hudson Trails Committee

Hiking

White Trail

4.1 mi away

0.3 mi long · Ossining

Hiking

Overlook Trail

4.1 mi away

0.7 mi long · Sleepy Hollow

Hiking Horses

Ridge Trail

4.2 mi away

0.9 mi long · Hawthorne

Hiking Horses

Pocantico River Trail

4.2 mi away

1.9 mi long · Sleepy Hollow

Hiking Horses

Big Tree Loop

4.2 mi away

1.1 mi long · Sleepy Hollow

Hiking Horses

Maple Loop

4.2 mi away

0.6 mi long · Sleepy Hollow

Hiking Horses

Spring Trail

4.3 mi away

0.7 mi long · Sleepy Hollow

Hiking Horses

Overlook Loop

4.3 mi away

0.9 mi long · Teatown Lake Reservation

Hiking

Rock Wall Loop

4.3 mi away

0.7 mi long · Hawthorne

Hiking Horses

Lucy's Loop

4.3 mi away

1.2 mi long · Hawthorne

Hiking Horses

Peggy's Way

4.3 mi away

0.6 mi long · Sleepy Hollow

Hiking Horses

Blue Trail (Main Loop)

4.3 mi away

3.1 mi long · Easy · Hawthorne

Hiking Biking Mountain biking

Farm Meadow Trail

4.3 mi away

0.8 mi long · Sleepy Hollow

Hiking Horses

Beech Trail

4.3 mi away

0.2 mi long · Easy · Croton on Hudson Trails Committee

Hiking

Red Trail

4.3 mi away

0.5 mi long · Sleepy Hollow

Hiking

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Nearby cities

All trails in New York

Common questions

How many trails are near Ossining?
We list 1,313 trails within 30 miles of Ossining, New York. This page shows the 60 closest.
What is the longest trail near Ossining?
Hudson Valley Greenway Trail (New Castle to Mahopac) is the longest on this page at about 16 miles, 3.3 miles from Ossining.
Are there dog-friendly trails near Ossining?
None of the trails on this page have a dog rule in our data yet. Check signs at the trailhead or the park's website.