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The Berkshires

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848 mi 1,365 km of trail 2 Runs

Gems 1 Gem Easy Trails 36 Trails Intermediate Trails 204 Trails Hard Trails 121 Trails
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Gems in The Berkshires - 1

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gem Favorite Big Bish Falls from above.

Bash Bish Falls

(1) Sheffield, MA

Runs in The Berkshires - 2

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Favorite Beautiful section of the AT just as the snow/ice was beginning to melt on the ridge
Difficult

Mount Greylock Summit Loop

6.6 mi 10.6 km • Loop • 2,252 ft Ascent 686.53 m Ascent

(10) Adams, MA
Favorite Views from Lenox Mountain summit.
Difficult

Ledges/Overbrook Loop

2.7 mi 4.3 km • Out and Back • 894 ft Ascent 272.42 m Ascent

(4) Lenox, MA

Trails in The Berkshires - 359

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89.7 mi 144.4 km #1AT: AMC - Berkshire Chapter (MA)
Intermediate
Sheffield, MA
Intermediate
89.7 mi 144.4 km Sheffield, MA
0.8 mi 1.2 km #2Ice Glen Trail
Intermediate
Stockbridge, MA
Intermediate
0.8 mi 1.2 km Stockbridge, MA
1.8 mi 3.0 km #3Thunderbolt Trail
Difficult
Adams, MA
Difficult
1.8 mi 3.0 km Adams, MA
2.7 mi 4.4 km #4Shaker Mountain Loop Trail
Difficult
Pittsfield, MA
Difficult
2.7 mi 4.4 km Pittsfield, MA
2.7 mi 4.3 km #5Hoosac Range Trail
Intermediate
North Adams, MA
Intermediate
2.7 mi 4.3 km North Adams, MA
2.7 mi 4.3 km #6Dome Trail
Difficult
Williamstown, MA
Difficult
2.7 mi 4.3 km Williamstown, MA
1.1 mi 1.7 km #7Cascade Trail
Intermediate
North Adams, MA
Intermediate
1.1 mi 1.7 km North Adams, MA
0.3 mi 0.5 km #8Ragged Mountain South Peak Trail
Difficult
Adams, MA
Difficult
0.3 mi 0.5 km Adams, MA
12.4 mi 20.0 km #9Ashuwillticook Rail Trail
Easy
Dalton, MA
Easy
12.4 mi 20.0 km Dalton, MA
0.5 mi 0.8 km #10March Cataract Trail
Difficult
Adams, MA
Difficult
0.5 mi 0.8 km Adams, MA
1.5 mi 2.5 km #11Old Mill Trail
Intermediate
Hinsdale, MA
Intermediate
1.5 mi 2.5 km Hinsdale, MA
0.7 mi 1.1 km #12Carriage Road
Easy
Pittsfield, MA
Easy
0.7 mi 1.1 km Pittsfield, MA
0.8 mi 1.3 km #13Gilmore Trail (Short Loop)
Intermediate
Otis, MA
Intermediate
0.8 mi 1.3 km Otis, MA
1.7 mi 2.7 km #14Blue Trail
Intermediate
Dalton, MA
Intermediate
1.7 mi 2.7 km Dalton, MA
0.3 mi 0.5 km #15Beaver Lodge Trail
Intermediate
Lenox, MA
Intermediate
0.3 mi 0.5 km Lenox, MA
2.1 mi 3.4 km #16Pine Cobble Trail
Difficult
Williamstown, MA
Difficult
2.1 mi 3.4 km Williamstown, MA
0.5 mi 0.9 km #17Tannery Falls Trail
Difficult
Adams, MA
Difficult
0.5 mi 0.9 km Adams, MA
2.9 mi 4.6 km #18Alander Mountain Trail
Difficult
Sheffield, MA
Difficult
2.9 mi 4.6 km Sheffield, MA
1.7 mi 2.8 km #19Race Brook Trail
Difficult
Sheffield, MA
Difficult
1.7 mi 2.8 km Sheffield, MA
2.7 mi 4.4 km #20Mt. Frissell Trail
Difficult
Canaan, CT
Difficult
2.7 mi 4.4 km Canaan, CT

Photos of The Berkshires - 98

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The trail requires crossing the river multiple times.
Mar 28, 2020 near Sheffield, MA
walk through pine trees forest at beginning of trail.
Mar 28, 2020 near Sheffield, MA
Views from Lenox Mountain summit.
Nov 18, 2016 near Lenox, MA
Overlook at the intersection of Mt. Prospect Trail and the Appalachian Trail, looking northwest over Williamstown.
Aug 10, 2019 near William…, MA
Tallest waterfall in MA
Mar 28, 2020 near Sheffield, MA
Race brook falls. Tallest waterfall in MA.
Mar 28, 2020 near Sheffield, MA
Questing Reservation meadow.
Jan 21, 2019 near New Mar…, MA
Deer Hill Falls
Dec 27, 2018 near Adams, MA

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