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Top Rated Trails
near South Windsor, Connecticut
South Windsor, Connecticut 
Recommended Routes, Photos, & More
11.6
mi
18.7
km
#1Glacier Ridge
Intermediate/Difficult
Farmingville, NY
|
Intermediate/Difficult
|
Farmingville, NY |
39
|
|
|
6.7
mi
10.8
km
#2Stillwell Woods
Intermediate/Difficult
Woodbury, NY
|
Intermediate/Difficult
|
Woodbury, NY |
38
|
|
4.2
mi
6.8
km
#3North Bethlehem Park Trail
Intermediate
McKownville, NY
|
Intermediate
|
McKownville, NY |
23
|
|
3.6
mi
5.8
km
#4Meadowlark
Difficult
Fort Salonga, NY
|
Difficult
|
Fort Salonga, NY |
25
|
|
|
4.1
mi
6.6
km
#5Western Greenway (Metropolitan Pwky to Beaver St)
Intermediate
Belmont, MA
|
Intermediate
|
Belmont, MA |
25
|
|
|
15.9
mi
25.6
km
#6East Setauket
Intermediate/Difficult
Terryville, NY
|
Intermediate/Difficult
|
Terryville, NY |
21
|
|
|
2.4
mi
3.9
km
#7Timbuktu
Intermediate/Difficult
Pleasant Valley, NY
|
Intermediate/Difficult
|
Pleasant Valley, NY |
5
|
|
|
1.5
mi
2.4
km
#8Orange Goose Loop
Difficult
Billerica, MA
|
Difficult
|
Billerica, MA |
7
|
|
|
1.8
mi
3.0
km
#9Byk Head
Intermediate
Pleasant Valley, NY
|
Intermediate
|
Pleasant Valley, NY |
4
|
|
|
0.6
mi
0.9
km
#10Coal Road Singletrack
Difficult
Belmont, MA
|
Difficult
|
Belmont, MA |
11
|
|
22.2
mi
35.8
km
#11Wallkill Valley Rail Trail
Easy
Wallkill, NY
|
Easy
|
Wallkill, NY |
6
|
|
|
0.7
mi
1.1
km
#12Orgasm
Difficult
Leominster, MA
|
Difficult
|
Leominster, MA |
3
|
|
|
4.4
mi
7.1
km
#13Shelton Lakes Recreation Path
Easy
Shelton, CT
|
Easy
|
Shelton, CT |
3
|
|
|
12.0
mi
19.3
km
#14Ashokan Rail Trail
Easy
West Hurley, NY
|
Easy
|
West Hurley, NY |
3
|
|
|
1.0
mi
1.6
km
#15Gumpus Trail
Difficult
Dracut, MA
|
Difficult
|
Dracut, MA |
3
|
|
|
0.3
mi
0.4
km
#16Hellevator
Difficult
Tyngsboro, MA
|
Difficult
|
Tyngsboro, MA |
3
|
|
|
1.0
mi
1.6
km
#17Green Apple
Intermediate/Difficult
Bellerose Terrace, NY
|
Intermediate/Difficult
|
Bellerose Terrace, NY |
3
|
|
|
1.3
mi
2.1
km
#18Northwest Trail
Difficult
Sharon, MA
|
Difficult
|
Sharon, MA |
3
|
|
|
0.6
mi
1.0
km
#19ORC
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.8
mi
1.2
km
#20Alter Ego
Difficult
Austerlitz, NY
|
Difficult
|
Austerlitz, NY |
3
|
|
|
0.7
mi
1.1
km
#21Bear Brook
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.5
mi
0.8
km
#22Ninja Test
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
1.1
mi
1.8
km
#23Morses Pond Trail
Intermediate
Wellesley, MA
|
Intermediate
|
Wellesley, MA |
2
|
|
|
0.3
mi
0.5
km
#24Fridge Door
Difficult
Bedford, MA
|
Difficult
|
Bedford, MA |
2
|
|
|
0.8
mi
1.4
km
#25DNA Trail
Intermediate
West Warwick, RI
|
Intermediate
|
West Warwick, RI |
2
|
|
|
1.4
mi
2.2
km
#26John Hand County Park Unmaintained Trail
Difficult
Croton-on-Hudson, NY
|
Difficult
|
Croton-on-Hudson, NY |
2
|
|
|
0.4
mi
0.7
km
#27Quarry Trail
Intermediate/Difficult
West Torrington, CT
|
Intermediate/Difficult
|
West Torrington, CT |
2
|
|
|
1.3
mi
2.0
km
#28Haunted Hollow
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
|
1.0
mi
1.6
km
#29Twister
Difficult
Granby, MA
|
Difficult
|
Granby, MA |
2
|
|
|
0.6
mi
1.0
km
#30Dirtfish
Difficult
Chatham, NY
|
Difficult
|
Chatham, NY |
2
|
