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Top Rated Trails
near Chesterfield, Massachusetts
Chesterfield, 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
|
|
|
1.8
mi
3.0
km
#5Byk Head
Intermediate
Pleasant Valley, NY
|
Intermediate
|
Pleasant Valley, NY |
4
|
|
22.2
mi
35.8
km
#6Wallkill Valley Rail Trail
Easy
Wallkill, NY
|
Easy
|
Wallkill, NY |
6
|
|
|
0.7
mi
1.1
km
#7Orgasm
Difficult
Leominster, MA
|
Difficult
|
Leominster, MA |
3
|
|
|
4.4
mi
7.1
km
#8Shelton Lakes Recreation Path
Easy
Shelton, CT
|
Easy
|
Shelton, CT |
3
|
|
|
12.0
mi
19.3
km
#9Ashokan Rail Trail
Easy
West Hurley, NY
|
Easy
|
West Hurley, NY |
3
|
|
|
1.0
mi
1.6
km
#10Gumpus Trail
Difficult
Dracut, MA
|
Difficult
|
Dracut, MA |
3
|
|
|
0.3
mi
0.4
km
#11Hellevator
Difficult
Tyngsboro, MA
|
Difficult
|
Tyngsboro, MA |
3
|
|
|
0.6
mi
1.0
km
#12ORC
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.8
mi
1.2
km
#13Alter Ego
Difficult
Austerlitz, NY
|
Difficult
|
Austerlitz, NY |
3
|
|
|
0.7
mi
1.1
km
#14Bear Brook
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.5
mi
0.8
km
#15Ninja Test
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
3
|
|
|
0.8
mi
1.4
km
#16DNA Trail
Intermediate
West Warwick, RI
|
Intermediate
|
West Warwick, RI |
2
|
|
|
0.4
mi
0.7
km
#17Quarry Trail
Intermediate/Difficult
West Torrington, CT
|
Intermediate/Difficult
|
West Torrington, CT |
2
|
|
|
1.3
mi
2.0
km
#18Haunted Hollow
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
|
1.0
mi
1.6
km
#19Twister
Difficult
Granby, MA
|
Difficult
|
Granby, MA |
2
|
|
|
0.6
mi
1.0
km
#20Dirtfish
Difficult
Chatham, NY
|
Difficult
|
Chatham, NY |
2
|
|
1.3
mi
2.1
km
#21Citizens Downhill
Very Difficult
Cairo, NY
|
Very Difficult
|
Cairo, NY |
2
|
|
|
1.5
mi
2.4
km
#22Pinnacle Trail
Intermediate
Austerlitz, NY
|
Intermediate
|
Austerlitz, NY |
2
|
|
|
1.3
mi
2.1
km
#23Solitude
Intermediate/Difficult
Chatham, NY
|
Intermediate/Difficult
|
Chatham, NY |
2
|
|
|
0.4
mi
0.7
km
#24Thrush
Intermediate
Tolland, CT
|
Intermediate
|
Tolland, CT |
2
|
|
|
0.6
mi
0.9
km
#25Billy Badger
Difficult
Charlemont, MA
|
Difficult
|
Charlemont, MA |
2
|
|
|
0.4
mi
0.6
km
#26Root Trail
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
|
1.5
mi
2.5
km
#27Upper Ledges
Intermediate
Poultney, VT
|
Intermediate
|
Poultney, VT |
2
|
|
|
0.9
mi
1.5
km
#28Lower Ledges
Intermediate
Poultney, VT
|
Intermediate
|
Poultney, VT |
2
|
|
|
0.4
mi
0.7
km
#29Hi Roller
Intermediate
Poultney, VT
|
Intermediate
|
Poultney, VT |
2
|
|
|
0.7
mi
1.2
km
#30Big Bear in Bear Brook State Park
Intermediate
Allenstown Elementary School, NH
|
Intermediate
|
Allenstown Elementary School, NH |
7
|
