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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 
4.4 mi 7.1 km #5Shelton Lakes Recreation Path
Easy Easy
Shelton, CT
Easy Easy
Shelton, CT
1.3 mi 2.1 km #6Northwest Trail
Difficult Difficult
Sharon, MA
Difficult Difficult
Sharon, MA
0.8 mi 1.4 km #7DNA Trail
Intermediate Intermediate
West Warwick, RI
Intermediate Intermediate
West Warwick, RI
0.4 mi 0.7 km #8Quarry Trail
Intermediate/Difficult Intermediate/Difficult
West Torrington, CT
Intermediate/Difficult Intermediate/Difficult
West Torrington, CT
1.3 mi 2.0 km #9Haunted Hollow
Difficult Difficult
Danielson, CT
Difficult Difficult
Danielson, CT
0.4 mi 0.7 km #10Thrush
Intermediate Intermediate
Tolland, CT
Intermediate Intermediate
Tolland, CT
0.4 mi 0.6 km #11Root Trail
Difficult Difficult
Danielson, CT
Difficult Difficult
Danielson, CT
25.5 mi 41.0 km #12Empire State Trail: Maybrook Trailway Section
Easy Easy
Brewster, NY
Easy Easy
Brewster, NY
1.1 mi 1.7 km #13Metacomet Trail: West Hartford Reservoir 6
Difficult Difficult
Weatogue, CT
Difficult Difficult
Weatogue, CT
23.4 mi 37.7 km #14Air Line State Park Trail
Easy Easy
East Hampton, CT
Easy Easy
East Hampton, CT
0.5 mi 0.7 km #15Goss Fields Trail
Easy Easy
Guilford, CT
Easy Easy
Guilford, CT
1.5 mi 2.4 km #16Bob's Trail
Difficult Difficult
Hebron, CT
Difficult Difficult
Hebron, CT
0.7 mi 1.1 km #17White Climb
Intermediate Intermediate
Cumberland, RI
Intermediate Intermediate
Cumberland, RI
1.2 mi 2.0 km #18Pachaug Trail to Hwy 138
Difficult Difficult
Preston City, CT
Difficult Difficult
Preston City, CT
0.8 mi 1.4 km #19Quarry Loop
Intermediate Intermediate
Easton, MA
Intermediate Intermediate
Easton, MA
0.4 mi 0.6 km #20Yellow Trail
Intermediate Intermediate
Cromwell, CT
Intermediate Intermediate
Cromwell, CT
2.1 mi 3.4 km #21Grand Trunk Trail
Easy Easy
Douglas, MA
Easy Easy
Douglas, MA
1.2 mi 1.9 km #22Run In / Run On Trail
Intermediate Intermediate
West Warwick, RI
Intermediate Intermediate
West Warwick, RI
0.6 mi 0.9 km #23Main Trail
Intermediate Intermediate
Brewster Hill, NY
Intermediate Intermediate
Brewster Hill, NY
1.0 mi 1.6 km #24Tomfoolery
Difficult Difficult
Danielson, CT
Difficult Difficult
Danielson, CT
1.0 mi 1.6 km #25Yellow Orange-Dotted (Evil Friends Loop)
Difficult Difficult
Old Bethpage, NY
Difficult Difficult
Old Bethpage, NY
0.8 mi 1.3 km #26Friends Trail
Difficult Difficult
Sharon, MA
Difficult Difficult
Sharon, MA
1.2 mi 1.9 km #27The Brickyard
Difficult Difficult
Old Bethpage, NY
Difficult Difficult
Old Bethpage, NY
0.7 mi 1.1 km #28Rejuvenation
Difficult Difficult
Danielson, CT
Difficult Difficult
Danielson, CT
0.5 mi 0.8 km #29DNR
Difficult Difficult
Danielson, CT
Difficult Difficult
Danielson, CT
0.3 mi 0.5 km #30Red Trail
Intermediate/Difficult Intermediate/Difficult
Guilford, CT
Intermediate/Difficult Intermediate/Difficult
Guilford, CT
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