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Top Rated Trails
near Williamsburg, Massachusetts
Williamsburg, Massachusetts 
Recommended Routes, Photos, & More
4.2
mi
6.8
km
#1North Bethlehem Park Trail
Intermediate
McKownville, NY
|
Intermediate
|
McKownville, NY |
23
|
|
3.4
mi
5.5
km
#2Hemlock
Intermediate/Difficult
Allenstown Elementary School, NH
|
Intermediate/Difficult
|
Allenstown Elementary School, NH |
16
|
|
0.9
mi
1.5
km
#3Berm-out
Difficult
Cairo, NY
|
Difficult
|
Cairo, NY |
8
|
|
|
2.4
mi
3.9
km
#4Timbuktu
Intermediate/Difficult
Pleasant Valley, NY
|
Intermediate/Difficult
|
Pleasant Valley, NY |
5
|
|
|
1.5
mi
2.4
km
#5Orange Goose Loop
Difficult
Billerica, MA
|
Difficult
|
Billerica, MA |
7
|
|
|
1.8
mi
3.0
km
#6Byk Head
Intermediate
Pleasant Valley, NY
|
Intermediate
|
Pleasant Valley, NY |
4
|
|
22.2
mi
35.8
km
#7Wallkill Valley Rail Trail
Easy
Wallkill, NY
|
Easy
|
Wallkill, NY |
6
|
|
|
0.7
mi
1.1
km
#8Orgasm
Difficult
Leominster, MA
|
Difficult
|
Leominster, MA |
3
|
|
|
4.4
mi
7.1
km
#9Shelton Lakes Recreation Path
Easy
Shelton, CT
|
Easy
|
Shelton, CT |
3
|
|
|
12.0
mi
19.3
km
#10Ashokan Rail Trail
Easy
West Hurley, NY
|
Easy
|
West Hurley, NY |
3
|
|
|
1.0
mi
1.6
km
#11Gumpus Trail
Difficult
Dracut, MA
|
Difficult
|
Dracut, MA |
3
|
|
|
0.3
mi
0.4
km
#12Hellevator
Difficult
Tyngsboro, MA
|
Difficult
|
Tyngsboro, MA |
3
|
|
|
0.6
mi
1.0
km
#13ORC
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.8
mi
1.2
km
#14Alter Ego
Difficult
Austerlitz, NY
|
Difficult
|
Austerlitz, NY |
3
|
|
|
0.7
mi
1.1
km
#15Bear Brook
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.5
mi
0.8
km
#16Ninja Test
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
1.1
mi
1.8
km
#17Morses Pond Trail
Intermediate
Wellesley, MA
|
Intermediate
|
Wellesley, MA |
2
|
|
|
0.8
mi
1.4
km
#18DNA Trail
Intermediate
West Warwick, RI
|
Intermediate
|
West Warwick, RI |
2
|
|
|
0.4
mi
0.7
km
#19Quarry Trail
Intermediate/Difficult
West Torrington, CT
|
Intermediate/Difficult
|
West Torrington, CT |
2
|
|
|
1.3
mi
2.0
km
#20Haunted Hollow
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
|
1.0
mi
1.6
km
#21Twister
Difficult
Granby, MA
|
Difficult
|
Granby, MA |
2
|
|
|
0.6
mi
1.0
km
#22Dirtfish
Difficult
Chatham, NY
|
Difficult
|
Chatham, NY |
2
|
|
|
1.5
mi
2.4
km
#23Pinnacle Trail
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
2
|
|
|
1.3
mi
2.1
km
#24Solitude
Intermediate/Difficult
Chatham, NY
|
Intermediate/Difficult
|
Chatham, NY |
2
|
|
|
0.4
mi
0.7
km
#25Thrush
Intermediate
Tolland, CT
|
Intermediate
|
Tolland, CT |
2
|
|
|
0.6
mi
0.9
km
#26Billy Badger
Difficult
Charlemont, MA
|
Difficult
|
Charlemont, MA |
2
|
|
|
0.4
mi
0.6
km
#27Root Trail
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
|
1.5
mi
2.5
km
#28Upper Ledges
Intermediate
Poultney, VT
|
Intermediate
|
Poultney, VT |
2
|
|
|
0.9
mi
1.5
km
#29Lower Ledges
Intermediate
Poultney, VT
|
Intermediate
|
Poultney, VT |
2
|
|
|
0.4
mi
0.7
km
#30Hi Roller
Intermediate
Poultney, VT
|
Intermediate
|
Poultney, VT |
2
|
