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Favorite Across the street from the parking lot at the trailhead in Cold Spring Harbor.  Near winter solstice.
Intermediate Intermediate

Nassau-Suffolk Trail

19.5 mi 31.3 km 945' Up 287.89 m Up 976' Down 297.41 m Down

Cold Sp…, NY
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Favorite Sturdy bridges span wetland sections of the trail, keeping feet dry in wet conditions.
Easy Easy

Norwalk River Valley Trail

2.0 mi 3.2 km 156' Up 47.41 m Up 18' Down 5.63 m Down

Wilton, CT
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Favorite The Ocean Loop Trail offers purely phenomenal views.
Easy Easy

Ocean View Loop Trail

1.5 mi 2.5 km 40' Up 12.19 m Up 36' Down 11.12 m Down

Newport, RI
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Favorite A scenic vista overlooking Saugatuck Reservoir.
Intermediate/Difficult Intermediate/Difficult

Saugatuck Trail

10.7 mi 17.3 km 907' Up 276.43 m Up 1,092' Down 332.76 m Down

Easton, CT
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Favorite Silent waters - Canoe Launch
Easy Easy

Shelton Lakes Recreation Path

4.4 mi 7.1 km 263' Up 80.29 m Up 223' Down 68.09 m Down

Shelton, CT
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Favorite View from the Tower
Easy/Intermediate Easy/Intermediate

Tower Trail

1.6 mi 2.5 km 512' Up 156.07 m Up 3' Down 0.94 m Down

Hamden, CT
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Favorite The Nepaug Dam
Easy Easy

Nepaug Dam Trail

1.0 mi 1.6 km 61' Up 18.51 m Up 75' Down 22.84 m Down

Collins…, CT
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Favorite The gateway to the Sunken Forest
Easy Easy

Sunken Forest Trail

1.5 mi 2.4 km 4' Up 1.09 m Up 4' Down 1.08 m Down

West Sa…, NY
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Favorite No Photos
Intermediate Intermediate

Horseneck Beach Loop

1.7 mi 2.8 km 29' Up 8.92 m Up 30' Down 9.1 m Down

Head of…, MA
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Favorite ADA Accessible Ramp - Law Park Walking Path
Easy Easy

Law Memorial Park Walking Path

0.4 mi 0.6 km 19' Up 5.83 m Up 16' Down 4.91 m Down

Briarcl…, NY
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Favorite No Photos
Easy Easy

Dutchess Rail Trail

15.0 mi 24.1 km 446' Up 135.82 m Up 471' Down 143.65 m Down

Hillsid…, NY
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Favorite No Photos
Intermediate Intermediate

Green Trail

1.0 mi 1.6 km 96' Up 29.28 m Up 83' Down 25.44 m Down

Goldens…, NY
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Favorite No Photos
Easy Easy

Harlem Valley Rail Trail: Ancram to Copake

5.3 mi 8.5 km 125' Up 38.08 m Up 149' Down 45.31 m Down

Boston…, NY
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Favorite Ferry Landing Boardwalk
Easy Easy

Ferry Landing Boardwalk

0.4 mi 0.7 km 6' Up 1.96 m Up 7' Down 2.16 m Down

Old Say…, CT
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Favorite No Photos
Easy Easy

Loop Trail

1.1 mi 1.8 km 121' Up 36.79 m Up 119' Down 36.38 m Down

Canton, MA
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Favorite No Photos
Easy Easy

Harlem Valley Rail Trail: Wassaic to Millerton

11.1 mi 17.9 km 360' Up 109.62 m Up 143' Down 43.46 m Down

Dover P…, NY
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Favorite The view across the reservoir in Wishnie Park
Easy Easy

Richard Wishnie Park Walking Path

0.3 mi 0.5 km 12' Up 3.74 m Up 11' Down 3.31 m Down

Ossining, NY
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Favorite Sunset on the Trolley Trail
Easy Easy

Trolley Trail

0.6 mi 1.0 km 46' Up 14.02 m Up 55' Down 16.76 m Down

Branfor…, CT
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Favorite 7SRR tunnel entrance
Easy/Intermediate Easy/Intermediate

Train Trail - East

0.4 mi 0.7 km 59' Up 17.86 m Up 43' Down 13.01 m Down

Chester…, CT
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Favorite No Photos
Easy Easy

Train Trail - West

0.8 mi 1.2 km 47' Up 14.24 m Up 42' Down 12.81 m Down

Chester…, CT
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Favorite No Photos
Intermediate Intermediate

Perimeter Trail

1.6 mi 2.6 km 190' Up 57.8 m Up 192' Down 58.67 m Down

Redding, CT
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Favorite No Photos
Easy Easy

13 Bridges Trail

2.1 mi 3.3 km 155' Up 47.11 m Up 153' Down 46.55 m Down

Sleepy…, NY
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Favorite Heublein Tower
Intermediate Intermediate

Yellow Trail

1.2 mi 1.9 km 362' Up 110.42 m Up 18' Down 5.37 m Down

Weatogue, CT
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Favorite Foggy morning on the Buxton Trestle.
Intermediate Intermediate

Long Island Greenbelt Trail

32.5 mi 52.3 km 971' Up 296.1 m Up 970' Down 295.64 m Down

Great R…, NY
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Favorite The "rope assist" section of Red Trail is one of the Park's most difficult sections.
Difficult Difficult

Red Trail

2.6 mi 4.2 km 476' Up 145.12 m Up 207' Down 63.06 m Down

Easton, CT
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Favorite Blue Trail at Fisherville Brook Wildlife Refuge.
Easy Easy

Blue Trail

1.2 mi 2.0 km 50' Up 15.29 m Up 51' Down 15.66 m Down

Exeter, RI
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Favorite Look for this tree marking the start point of the trail.
Intermediate Intermediate

Northwest Path

5.2 mi 8.4 km 249' Up 75.87 m Up 314' Down 95.73 m Down

Sag Harbor, NY
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Favorite Weir Pond Trail, at the beginning (or end!) of the loop.
Easy/Intermediate Easy/Intermediate

Pond Loop Trail

0.7 mi 1.1 km 14' Up 4.37 m Up 64' Down 19.62 m Down

Georgetown, CT
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Favorite Big Bish Falls from above.
Easy/Intermediate Easy/Intermediate

Bash Bish Falls Trail

0.8 mi 1.2 km 215' Up 65.46 m Up 21' Down 6.39 m Down

Boston…, NY
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Favorite If the snow is too deep for foot travel along the Turner Reservoir, cross-country skiing makes for a great alternative.
Easy/Intermediate Easy/Intermediate

Turner Reservoir Loop Trail

2.9 mi 4.7 km 43' Up 13.18 m Up 44' Down 13.33 m Down

East Pr…, RI
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