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Top Rated Trails
near Sleepy Hollow Lake, New York
Sleepy Hollow Lake, New York 
Recommended Routes, Photos, & More
4.2
mi
6.8
km
#1North Bethlehem Park Trail
Intermediate
McKownville, NY
|
Intermediate
|
McKownville, NY |
22
|
|
0.9
mi
1.5
km
#2Berm-out
Difficult
Cairo, NY
|
Difficult
|
Cairo, NY |
8
|
|
2.4
mi
3.9
km
#3Timbuktu
Intermediate/Difficult
Pleasant Valley, NY
|
Intermediate/Difficult
|
Pleasant Valley, NY |
5
|
|
|
1.8
mi
3.0
km
#4Byk Head
Intermediate
Pleasant Valley, NY
|
Intermediate
|
Pleasant Valley, NY |
4
|
|
22.2
mi
35.8
km
#5Wallkill Valley Rail Trail
Easy
Wallkill, NY
|
Easy
|
Wallkill, NY |
6
|
|
|
4.4
mi
7.1
km
#6Shelton Lakes Recreation Path
Easy
Shelton, CT
|
Easy
|
Shelton, CT |
3
|
|
|
12.0
mi
19.3
km
#7Ashokan Rail Trail
Easy
West Hurley, NY
|
Easy
|
West Hurley, NY |
3
|
|
|
0.6
mi
1.0
km
#8ORC
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.8
mi
1.2
km
#9Alter Ego
Difficult
Austerlitz, NY
|
Difficult
|
Austerlitz, NY |
3
|
|
|
0.7
mi
1.1
km
#10Bear Brook
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.5
mi
0.8
km
#11Ninja Test
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
1.4
mi
2.2
km
#12John Hand County Park Unmaintained Trail
Difficult
Croton-on-Hudson, NY
|
Difficult
|
Croton-on-Hudson, NY |
2
|
|
|
0.4
mi
0.7
km
#13Quarry Trail
Intermediate/Difficult
West Torrington, CT
|
Intermediate/Difficult
|
West Torrington, CT |
2
|
|
|
1.0
mi
1.6
km
#14Twister
Difficult
Granby, MA
|
Difficult
|
Granby, MA |
2
|
|
|
0.6
mi
1.0
km
#15Dirtfish
Difficult
Chatham, NY
|
Difficult
|
Chatham, NY |
2
|
|
|
0.5
mi
0.8
km
#16Bailey's
Difficult
Peekskill, NY
|
Difficult
|
Peekskill, NY |
2
|
|
1.3
mi
2.1
km
#17Citizens Downhill
Very Difficult
Cairo, NY
|
Very Difficult
|
Cairo, NY |
2
|
|
|
1.5
mi
2.4
km
#18Pinnacle Trail
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
2
|
|
|
1.3
mi
2.1
km
#19Solitude
Intermediate/Difficult
Chatham, NY
|
Intermediate/Difficult
|
Chatham, NY |
2
|
|
|
0.4
mi
0.7
km
#20Thrush
Intermediate
Tolland, CT
|
Intermediate
|
Tolland, CT |
2
|
|
|
0.6
mi
0.9
km
#21Billy Badger
Difficult
Charlemont, MA
|
Difficult
|
Charlemont, MA |
2
|
|
|
1.9
mi
3.0
km
#22On Your Marc
Very Difficult
Buchanan, NY
|
Very Difficult
|
Buchanan, NY |
2
|
|
|
0.3
mi
0.5
km
#23Ambush
Very Difficult
Gloversville, NY
|
Very Difficult
|
Gloversville, NY |
2
|
|
|
0.7
mi
1.1
km
#24Forever Wild
Intermediate/Difficult
Gloversville, NY
|
Intermediate/Difficult
|
Gloversville, NY |
2
|
|
|
25.5
mi
41.0
km
#25Empire State Trail: Maybrook Trailway Section
Easy
Brewster, NY
|
Easy
|
Brewster, NY |
1
|
|
|
1.1
mi
1.7
km
#26Metacomet Trail: West Hartford Reservoir 6
Difficult
Weatogue, CT
|
Difficult
|
Weatogue, CT |
1
|
|
|
0.6
mi
1.0
km
#27Poet's Seat Tower Access Road
Intermediate
Greenfield, MA
|
Intermediate
|
Greenfield, MA |
1
|
|
|
23.4
mi
37.7
km
#28Air Line State Park Trail
Easy
East Hampton, CT
|
Easy
|
East Hampton, CT |
1
|
|
|
2.2
mi
3.6
km
#29Red Line
Difficult
Northampton, MA
|
Difficult
|
Northampton, MA |
1
|
|
|
1.0
mi
1.6
km
#30Jacob's Ladder
Very Difficult
Granby, MA
|
Very Difficult
|
Granby, MA |
1
|
