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The Berkshires

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Gems in The Berkshires - 2

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gem Favorite Campbell Falls

Campbell Falls

(1) New Mar…, MA
gem Favorite Big Bish Falls from above.

Bash Bish Falls

(3) Sheffield, MA

Recommended Routes in The Berkshires - 4

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Favorite Views from Lenox Mountain summit.
Difficult

Ledges/Overbrook Loop

2.7 mi 4.3 km 894' Up 272.42 m Up 898' Down 273.68 m Down

Lenox, MA
Favorite Mt Greylock and the shiny tower on top.
Intermediate/Difficult

Mount Greylock Summit Loop

6.6 mi 10.7 km 2,251' Up 686.23 m Up 2,246' Down 684.66 m Down

Adams, MA
Favorite Microspikes recommended icy winter conditions (these crampons/ice axe are overkill).
Intermediate/Difficult

Bellows Pipe to Mt Greylock Summit

5.8 mi 9.4 km 2,231' Up 679.9 m Up 2,231' Down 679.86 m Down

Adams, MA
Favorite View from Mt. Frissel looking Southeast
Intermediate/Difficult

CT State Highpoint/Tri-point Out and Back

2.9 mi 4.7 km 1,045' Up 318.64 m Up 1,045' Down 318.48 m Down

Salisbury, CT

The Berkshires Hiking

  • 1,007 Miles 1,621 Kilometers of Trail
  • 4 Recommended Routes
  • 2 Gems Gems
  • 163 Easy Trails Easy Trails
  • 405 Intermediate Trails Intermediate Trails
  • 148 Difficult Trails Difficult Trails
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Areas Within The Berkshires

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Trails in The Berkshires - 712

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1.3 mi 2.1 km #1Widow White Trail
Difficult
Lanesborough, MA
Difficult
Lanesborough, MA
4.7 mi 7.6 km #2Wildcat Trail
Intermediate
Stockbridge, MA
Intermediate
Stockbridge, MA
1.8 mi 2.9 km #3Pond Loop Trail
Easy
Great Barrington, MA
Easy
Great Barrington, MA
5.2 mi 8.4 km #4Beartown Mountain Trail
Intermediate
Great Barrington, MA
Intermediate
Great Barrington, MA
1.6 mi 2.6 km #5Beebe Trail
Intermediate
Stockbridge, MA
Intermediate
Stockbridge, MA
2.4 mi 3.8 km #6Yokun Ridge Trail
Intermediate
Lenox, MA
Intermediate
Lenox, MA
0.4 mi 0.7 km #7Secret Trail
Intermediate/Difficult
Lenox, MA
Intermediate/Difficult
Lenox, MA
0.8 mi 1.2 km #8Vista Trail
Intermediate/Difficult
Lenox, MA
Intermediate/Difficult
Lenox, MA
0.9 mi 1.5 km #9Mahanna Cobble Trail
Intermediate/Difficult
Lenox, MA
Intermediate/Difficult
Lenox, MA
1.2 mi 1.9 km #10Bosquet Connector Trail
Easy/Intermediate
Pittsfield, MA
Easy/Intermediate
Pittsfield, MA

Photos of The Berkshires - 148

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Winter backpacking at Alander Mountain.
Apr 22, 2015 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
walk through pine trees forest at beginning of trail.
Mar 28, 2020 near Sheffield, MA
Nice camping spot, fire pits, outhouse, and tent platforms.
Mar 28, 2020 near Sheffield, MA
The trail requires crossing the river multiple times.
Mar 28, 2020 near Sheffield, MA
Tallest waterfall in MA
Mar 28, 2020 near Sheffield, MA
Titmouse in a tree.
Feb 9, 2023 near William…, MA