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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 Levy Preserve Merrick, Long Island, NY
Easy/Intermediate Easy/Intermediate

Norman J. Levy Outer Loop

1.7 mi 2.7 km 35' Up 10.76 m Up 31' Down 9.45 m Down

Freeport, NY
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Favorite No Photos
Intermediate Intermediate

Fox Hollow Main Trail

0.5 mi 0.9 km 70' Up 21.43 m Up 54' Down 16.51 m Down

Laurel…, NY
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Favorite Manorville Hills
Intermediate Intermediate

Manorville Hills

9.8 mi 15.8 km 691' Up 210.55 m Up 599' Down 182.45 m Down

Manorville, NY
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Favorite A nice little section of the Saugatuck Trail.
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 No Photos
Easy Easy

Empire State Trail: Maybrook Trailway Section

25.5 mi 41.0 km 444' Up 135.43 m Up 615' Down 187.43 m Down

Brewster, NY
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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 No Photos
Difficult Difficult

Lion's Head Trail

1.2 mi 2.0 km 576' Up 175.49 m Up 77' Down 23.38 m Down

Canaan, CT
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Favorite A fork in the road.
Intermediate Intermediate

Sammy C Trail

3.2 mi 5.2 km 254' Up 77.47 m Up 264' Down 80.39 m Down

Charles…, RI
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Favorite Tight spot!  On the Kettletown Blue Trail South Lap
Difficult Difficult

Pomperaug Trail - Blue

1.7 mi 2.7 km 307' Up 93.56 m Up 173' Down 52.76 m Down

Southbury, CT
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Favorite The east end of the Yellow Trail in early fall.
Intermediate Intermediate

Yellow Trail

2.2 mi 3.6 km 501' Up 152.56 m Up 249' Down 75.94 m Down

Hamden, CT
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Favorite Unnamed falls on Day Pond Brook
Intermediate Intermediate

Day Pond Brook Spur Trail

0.2 mi 0.4 km 1' Up 0.19 m Up 88' Down 26.89 m Down

East Ha…, CT
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Favorite Field along the Yellow Trail in Mashomack Preserve
Easy/Intermediate Easy/Intermediate

Yellow Trail

1.0 mi 1.7 km 88' Up 26.79 m Up 45' Down 13.63 m Down

Shelter…, NY
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Favorite No Photos
Easy Easy

Norwalk River Valley Trail: Redding Mile

0.8 mi 1.3 km 20' Up 5.98 m Up 69' Down 20.98 m Down

Ridgefield, CT
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Favorite Meadow Trail
Intermediate/Difficult Intermediate/Difficult

Naugatuck (Blue) Trail

11.6 mi 18.6 km 962' Up 293.28 m Up 1,073' Down 327.03 m Down

Woodbridge, CT
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Favorite picnic area
Easy Easy

Orient Beach Lighthouse Trail

2.8 mi 4.5 km 8' Up 2.52 m Up 11' Down 3.41 m Down

Greenport, NY
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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 You're pretty far along by the time you make it to this sign.
Difficult Difficult

Glacier Ridge

11.6 mi 18.7 km 936' Up 285.25 m Up 936' Down 285.3 m Down

Farming…, NY
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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 No Photos
Difficult Difficult

Meadowlark Trail

3.6 mi 5.8 km 175' Up 53.45 m Up 178' Down 54.19 m Down

Fort Sa…, NY
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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 Horses and buttercups
Difficult Difficult

Yellow Trail

2.0 mi 3.3 km 8' Up 2.58 m Up 94' Down 28.56 m Down

Tiverton, RI
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Favorite Beaver Brook is quite verdant in the spring.
Easy Easy

Louis C. Clark Sanctuary

0.3 mi 0.6 km 9' Up 2.63 m Up 19' Down 5.76 m Down

Glen Head, NY
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Favorite No Photos
Intermediate Intermediate

Meyer Aqueduct Trail

0.5 mi 0.8 km 17' Up 5.03 m Up 15' Down 4.66 m Down

Armonk, NY
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Favorite No Photos
Easy Easy

Winslow Dog Park Outer Loop

0.5 mi 0.9 km 24' Up 7.33 m Up 27' Down 8.12 m Down

Westport, CT
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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 Second Boardwalk
Intermediate Intermediate

Red Trail

2.1 mi 3.4 km 89' Up 27.1 m Up 69' Down 20.92 m Down

Bliss C…, MA
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