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11.6 mi 18.7 km #1Glacier Ridge
Intermediate/Difficult Intermediate/Difficult
Farmingville, NY
Intermediate/Difficult Intermediate/Difficult
Farmingville, NY 38 
6.7 mi 10.8 km #2Stillwell Woods
Intermediate/Difficult Intermediate/Difficult
Woodbury, NY
Intermediate/Difficult Intermediate/Difficult
Woodbury, NY 37 
3.6 mi 5.8 km #3Meadowlark
Difficult Difficult
Fort Salonga, NY
Difficult Difficult
Fort Salonga, NY 25 
15.9 mi 25.6 km #4East Setauket
Intermediate/Difficult Intermediate/Difficult
Terryville, NY
Intermediate/Difficult Intermediate/Difficult
Terryville, NY 21 
2.4 mi 3.9 km #5Timbuktu
Intermediate/Difficult Intermediate/Difficult
Pleasant Valley, NY
Intermediate/Difficult Intermediate/Difficult
Pleasant Valley, NY
1.8 mi 3.0 km #6Byk Head
Intermediate Intermediate
Pleasant Valley, NY
Intermediate Intermediate
Pleasant Valley, NY
4.4 mi 7.1 km #7Shelton Lakes Recreation Path
Easy Easy
Shelton, CT
Easy Easy
Shelton, CT
1.0 mi 1.6 km #8Green Apple
Intermediate/Difficult Intermediate/Difficult
Bellerose Terrace, NY
Intermediate/Difficult Intermediate/Difficult
Bellerose Terrace, NY
1.3 mi 2.1 km #9Northwest Trail
Difficult Difficult
Sharon, MA
Difficult Difficult
Sharon, MA
0.6 mi 1.0 km #10Rogue Dead Guy
Difficult Difficult
Cohasset, MA
Difficult Difficult
Cohasset, MA
0.8 mi 1.4 km #11DNA Trail
Intermediate Intermediate
West Warwick, RI
Intermediate Intermediate
West Warwick, RI
0.4 mi 0.7 km #12Quarry Trail
Intermediate/Difficult Intermediate/Difficult
West Torrington, CT
Intermediate/Difficult Intermediate/Difficult
West Torrington, CT
1.3 mi 2.0 km #13Haunted Hollow
Difficult Difficult
Danielson, CT
Difficult Difficult
Danielson, CT
0.4 mi 0.7 km #14Thrush
Intermediate Intermediate
Tolland, CT
Intermediate Intermediate
Tolland, CT
0.4 mi 0.6 km #15Root Trail
Difficult Difficult
Danielson, CT
Difficult Difficult
Danielson, CT
25.5 mi 41.0 km #16Empire State Trail: Maybrook Trailway Section
Easy Easy
Brewster, NY
Easy Easy
Brewster, NY
1.1 mi 1.7 km #17Metacomet Trail: West Hartford Reservoir 6
Difficult Difficult
Weatogue, CT
Difficult Difficult
Weatogue, CT
23.4 mi 37.7 km #18Air Line State Park Trail
Easy Easy
East Hampton, CT
Easy Easy
East Hampton, CT
2.2 mi 3.6 km #19Peabody Loop
Intermediate Intermediate
Dover, MA
Intermediate Intermediate
Dover, MA
0.5 mi 0.7 km #20Goss Fields Trail
Easy Easy
Guilford, CT
Easy Easy
Guilford, CT
1.5 mi 2.4 km #21Bob's Trail
Difficult Difficult
Hebron, CT
Difficult Difficult
Hebron, CT
0.7 mi 1.1 km #22White Climb
Intermediate Intermediate
Cumberland, RI
Intermediate Intermediate
Cumberland, RI
1.2 mi 2.0 km #23Pachaug Trail to Hwy 138
Difficult Difficult
Preston City, CT
Difficult Difficult
Preston City, CT
0.8 mi 1.4 km #24Quarry Loop
Intermediate Intermediate
Easton, MA
Intermediate Intermediate
Easton, MA
0.4 mi 0.6 km #25Yellow Trail
Intermediate Intermediate
Cromwell, CT
Intermediate Intermediate
Cromwell, CT
2.1 mi 3.4 km #26Grand Trunk Trail
Easy Easy
Douglas, MA
Easy Easy
Douglas, MA
1.2 mi 1.9 km #27Run In / Run On Trail
Intermediate Intermediate
West Warwick, RI
Intermediate Intermediate
West Warwick, RI
0.6 mi 0.9 km #28Main Trail
Intermediate Intermediate
Brewster Hill, NY
Intermediate Intermediate
Brewster Hill, NY
1.0 mi 1.6 km #29Tomfoolery
Difficult Difficult
Danielson, CT
Difficult Difficult
Danielson, CT
1.0 mi 1.6 km #30Yellow Orange-Dotted (Evil Friends Loop)
Difficult Difficult
Old Bethpage, NY
Difficult Difficult
Old Bethpage, NY
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