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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 Dog walking is a popular activity on the Norwalk River Valley Trail.
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 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

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 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 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 Looking out to the water.
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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Favorite Rewarding view after a steep climb!
Intermediate Intermediate

Highland Trail (Pink)

1.2 mi 1.9 km 194' Up 59.17 m Up 170' Down 51.88 m Down

Manchester, CT
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Favorite Mondo Pond Trail view of the largest pond
Easy/Intermediate Easy/Intermediate

Mondo Ponds Trail

0.9 mi 1.5 km 22' Up 6.62 m Up 22' Down 6.61 m Down

City of…, CT
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Favorite No Photos
Intermediate Intermediate

Putnam County Trailway

11.8 mi 19.1 km 619' Up 188.61 m Up 412' Down 125.51 m Down

Brewster, NY
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Favorite The trail on a former rail bridge over the Farmington River
Easy Easy

Farmington Canal Heritage Trail: Northern Connecticut Section

22.8 mi 36.7 km 614' Up 187.26 m Up 598' Down 182.33 m Down

North G…, CT
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Favorite West Thompson Lake makes for a great view along the Shoreline Trail.
Easy Easy

Shoreline Trail

4.1 mi 6.5 km 91' Up 27.66 m Up 85' Down 25.85 m Down

North G…, CT
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