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Ossining

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Recommended Routes in Ossining - 3

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Favorite No Photos
Easy 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
Explore in 3D
Favorite Boggy pond with lots of damsel flies.
Intermediate Intermediate

Pocantico Park Loop

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

Briarcl…, NY
Explore in 3D
Favorite My favorite bit of the Lakeside Trail
Intermediate Intermediate

Teatown Lake Cliffdale Farm Double Loop

6.2 mi 10.0 km 519' Up 158.14 m Up 504' Down 153.67 m Down

Croton-…, NY
Explore in 3D

Ossining Running

  • 39 Miles 63 Kilometers of Trail
  • 3 Recommended Routes
  • 5 Easy Trails Easy Trails
  • 8 Intermediate Trails Intermediate Trails
  • 2 Difficult Trails Difficult Trails
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Areas Within Ossining

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Trails in Ossining - 12

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1.9 mi 3.1 km #1North County Trailway: Law Park South to Route 117
Intermediate Intermediate
Briarcliff Manor, NY
Intermediate Intermediate
Briarcliff Manor, NY
0.4 mi 0.6 km #2Law Memorial Park Walking Path
Easy Easy
Briarcliff Manor, NY
Easy Easy
Briarcliff Manor, NY
0.3 mi 0.5 km #3Richard Wishnie Park Walking Path
Easy Easy
Ossining, NY
Easy Easy
Ossining, NY
27.8 mi 44.7 km #4Old Croton Aqueduct Trail
Easy/Intermediate Easy/Intermediate
Croton-on-Hudson, NY
Easy/Intermediate Easy/Intermediate
Croton-on-Hudson, NY
0.9 mi 1.5 km #5Kate Kennard Trail
Intermediate Intermediate
Briarcliff Manor, NY
Intermediate Intermediate
Briarcliff Manor, NY
2.3 mi 3.7 km #6North County Trailway: Law Park North to North State Road/Rte.…
Intermediate Intermediate
Briarcliff Manor, NY
Intermediate Intermediate
Briarcliff Manor, NY
0.4 mi 0.6 km #7Yellow Trail
Difficult Difficult
Briarcliff Manor, NY
Difficult Difficult
Briarcliff Manor, NY
0.6 mi 0.9 km #8Red Trail
Difficult Difficult
Briarcliff Manor, NY
Difficult Difficult
Briarcliff Manor, NY
1.7 mi 2.8 km #9Cliffdale Loop
Intermediate Intermediate
Croton-on-Hudson, NY
Intermediate Intermediate
Croton-on-Hudson, NY
1.6 mi 2.7 km #10Lakeside Loop
Easy Easy
Croton-on-Hudson, NY
Easy Easy
Croton-on-Hudson, NY
1.1 mi 1.8 km #11Cliffdale-Teatown Trail
Intermediate Intermediate
Croton-on-Hudson, NY
Intermediate Intermediate
Croton-on-Hudson, NY

Photos of Ossining - 45

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

Croton Dam
Feb 1, 2019 near Croton-…, NY
Croton Dam spillway from Croton Point Park
Feb 1, 2019 near Croton-…, NY
Waterfall in Teatown towards the end of the trail.
May 21, 2019 near Croton-…, NY
ADA Accessible Ramp - Law Park Walking Path
Sep 23, 2019 near Briarcl…, NY
Law Park Pond in the summer
Sep 23, 2019 near Briarcl…, NY
My favorite bit of the Lakeside Trail
Aug 15, 2020 near Croton-…, NY
Old Farm Field
Aug 16, 2020 near Croton-…, NY
Teatown Lake Boardwalk
Aug 16, 2020 near Croton-…, NY
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