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Top Rated Trails
near Montauk, New York
Montauk, New York 
Recommended Routes, Photos, & More
11.6
mi
18.7
km
#1Glacier Ridge
Intermediate/Difficult
Farmingville, NY
|
Intermediate/Difficult
|
Farmingville, NY |
38
|
|
3.6
mi
5.8
km
#2Meadowlark
Difficult
Fort Salonga, NY
|
Difficult
|
Fort Salonga, NY |
25
|
|
|
15.9
mi
25.6
km
#3East Setauket
Intermediate/Difficult
Terryville, NY
|
Intermediate/Difficult
|
Terryville, NY |
21
|
|
4.4
mi
7.1
km
#4Shelton Lakes Recreation Path
Easy
Shelton, CT
|
Easy
|
Shelton, CT |
3
|
|
2.7
mi
4.3
km
#5Moraine Trail - Northern Section
Intermediate
West Falmouth, MA
|
Intermediate
|
West Falmouth, MA |
3
|
|
|
1.3
mi
2.1
km
#6Northwest Trail
Difficult
Sharon, MA
|
Difficult
|
Sharon, MA |
3
|
|
|
0.8
mi
1.4
km
#7DNA Trail
Intermediate
West Warwick, RI
|
Intermediate
|
West Warwick, RI |
2
|
|
|
0.4
mi
0.7
km
#8Quarry Trail
Intermediate/Difficult
West Torrington, CT
|
Intermediate/Difficult
|
West Torrington, CT |
2
|
|
|
1.3
mi
2.0
km
#9Haunted Hollow
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
1.2
mi
1.9
km
#10Moose Alley
Easy/Intermediate
Pocasset, MA
|
Easy/Intermediate
|
Pocasset, MA |
2
|
|
|
0.4
mi
0.7
km
#11Thrush
Intermediate
Tolland, CT
|
Intermediate
|
Tolland, CT |
2
|
|
|
0.4
mi
0.6
km
#12Root Trail
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
|
1.1
mi
1.7
km
#13Metacomet Trail: West Hartford Reservoir 6
Difficult
Weatogue, CT
|
Difficult
|
Weatogue, CT |
1
|
|
|
23.4
mi
37.7
km
#14Air Line State Park Trail
Easy
East Hampton, CT
|
Easy
|
East Hampton, CT |
1
|
|
|
0.4
mi
0.7
km
#15Doggy Trail
Intermediate
North Falmouth, MA
|
Intermediate
|
North Falmouth, MA |
1
|
|
|
0.6
mi
1.0
km
#16Graveyard
Difficult
North Falmouth, MA
|
Difficult
|
North Falmouth, MA |
1
|
|
|
1.5
mi
2.4
km
#17Bob's Trail
Difficult
Hebron, CT
|
Difficult
|
Hebron, CT |
1
|
|
|
0.5
mi
0.7
km
#18Goss Fields Trail
Easy
Guilford, CT
|
Easy
|
Guilford, CT |
1
|
|
|
0.7
mi
1.1
km
#19White Climb
Intermediate
Cumberland, RI
|
Intermediate
|
Cumberland, RI |
1
|
|
|
0.4
mi
0.7
km
#20Hangover
Difficult
North Falmouth, MA
|
Difficult
|
North Falmouth, MA |
1
|
|
|
1.2
mi
2.0
km
#21Pachaug Trail to Hwy 138
Difficult
Preston City, CT
|
Difficult
|
Preston City, CT |
1
|
|
|
0.8
mi
1.4
km
#22Quarry Loop
Intermediate
Easton, MA
|
Intermediate
|
Easton, MA |
1
|
|
|
0.4
mi
0.6
km
#23Yellow Trail
Intermediate
Cromwell, CT
|
Intermediate
|
Cromwell, CT |
1
|
|
|
1.0
mi
1.6
km
#24Lost Trail
Intermediate
North Falmouth, MA
|
Intermediate
|
North Falmouth, MA |
1
|
|
|
1.1
mi
1.8
km
#25Cosmos
Intermediate
Pocasset, MA
|
Intermediate
|
Pocasset, MA |
1
|
|
|
1.2
mi
1.9
km
#26Run In / Run On Trail
Intermediate
West Warwick, RI
|
Intermediate
|
West Warwick, RI |
1
|
|
|
2.1
mi
3.4
km
#27Grand Trunk Trail
Easy
Douglas, MA
|
Easy
|
Douglas, MA |
1
|
|
|
1.0
mi
1.6
km
#28Tomfoolery
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
1
|
|
|
0.5
mi
0.7
km
#29Tombstone Trail
Intermediate
North Falmouth, MA
|
Intermediate
|
North Falmouth, MA |
1
|
|
|
1.0
mi
1.6
km
#30Hare and Hound
Intermediate
North Falmouth, MA
|
Intermediate
|
North Falmouth, MA |
1
|
