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Particularly Special Place
Top Rated Hiking Trails
near Montauk, New York
Montauk, New York 
Recommended Routes, Photos, & More
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
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
Intermediate/Difficult
AT: AMC - Berkshire Chapter (MA)
89.7 mi 144.4 km • 15,444' Up 4707.35 m Up • 14,639' Down 4461.95 m Down
Sheffield, MA
Intermediate
Manorville Hills
9.8 mi 15.8 km • 691' Up 210.55 m Up • 599' Down 182.45 m Down
Manorville, NY
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
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
No Photos
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
Intermediate
Sammy C Trail
3.2 mi 5.2 km • 254' Up 77.47 m Up • 264' Down 80.39 m Down
Charles…, RI
Difficult
Pomperaug Trail - Blue
1.7 mi 2.7 km • 307' Up 93.56 m Up • 173' Down 52.76 m Down
Southbury, CT
Intermediate
Yellow Trail
2.2 mi 3.6 km • 501' Up 152.56 m Up • 249' Down 75.94 m Down
Hamden, CT
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
Easy/Intermediate
Yellow Trail
1.0 mi 1.7 km • 88' Up 26.79 m Up • 45' Down 13.63 m Down
Shelter…, NY
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
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
Easy/Intermediate
Tower Trail
1.6 mi 2.5 km • 512' Up 156.07 m Up • 3' Down 0.94 m Down
Hamden, CT
Difficult
Glacier Ridge
11.6 mi 18.7 km • 936' Up 285.25 m Up • 936' Down 285.3 m Down
Farming…, NY
Easy
Nepaug Dam Trail
1.0 mi 1.6 km • 61' Up 18.51 m Up • 75' Down 22.84 m Down
Collins…, CT
No Photos
Intermediate
Moraine Trail - Northern Section
2.7 mi 4.3 km • 208' Up 63.25 m Up • 244' Down 74.33 m Down
West Fa…, MA
No Photos
Difficult
Meadowlark Trail
3.6 mi 5.8 km • 175' Up 53.45 m Up • 178' Down 54.19 m Down
Fort Sa…, NY
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
No Photos
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
Difficult
Yellow Trail
2.0 mi 3.3 km • 8' Up 2.58 m Up • 94' Down 28.56 m Down
Tiverton, RI
No Photos
Intermediate
Gilmore Trail (Short Loop)
0.8 mi 1.3 km • 113' Up 34.37 m Up • 109' Down 33.13 m Down
Otis, MA
No Photos
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
Intermediate
Red Trail
2.1 mi 3.4 km • 89' Up 27.1 m Up • 69' Down 20.92 m Down
Bliss C…, MA
Difficult
Crest Trail - Blue/White
1.7 mi 2.8 km • 312' Up 95.16 m Up • 223' Down 67.91 m Down
Southbury, CT
Easy/Intermediate
Canonchet Trail
2.9 mi 4.7 km • 122' Up 37.25 m Up • 317' Down 96.73 m Down
Hopkinton, RI
No Photos
Difficult
Quarry Trail
0.4 mi 0.7 km • 101' Up 30.93 m Up • 4' Down 1.08 m Down
West To…, CT
