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Monterey

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  3. The Berkshires
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Trails in Monterey - 25

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5.2 mi 8.4 km #1Mount Wilcox Trail
Intermediate Intermediate
Great Barrington, MA
Intermediate Intermediate
Great Barrington, MA 1 
3.3 mi 5.4 km #2Sky Peak Trail East
Intermediate Intermediate
Lee, MA
Intermediate Intermediate
Lee, MA 1 
1.8 mi 2.9 km #3Pond Loop Trail
Easy Easy
Great Barrington, MA
Easy Easy
Great Barrington, MA 1 
4.7 mi 7.6 km #4Wildcat Trail
Intermediate Intermediate
Stockbridge, MA
Intermediate Intermediate
Stockbridge, MA 1 
2.0 mi 3.2 km #5Cobble Loop Trail
Difficult Difficult
Lee, MA
Difficult Difficult
Lee, MA 1 
5.2 mi 8.4 km #6Beartown Mountain Trail
Intermediate Intermediate
Great Barrington, MA
Intermediate Intermediate
Great Barrington, MA 1 
3.6 mi 5.9 km #7Turkey Trail
Intermediate Intermediate
Great Barrington, MA
Intermediate Intermediate
Great Barrington, MA 1 
1.6 mi 2.6 km #8Beebe Trail
Intermediate Intermediate
Stockbridge, MA
Intermediate Intermediate
Stockbridge, MA 1 
1.2 mi 1.9 km #9Sky Peak Trail West
Easy Easy
Lee, MA
Easy Easy
Lee, MA 1 
3.1 mi 5.0 km #10Airplane Trail
Intermediate Intermediate
Lee, MA
Intermediate Intermediate
Lee, MA 1 

Photos of Monterey - 16

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Wildcat Shelter
Mar 29, 2020 near Great B…, MA
Stone wall on the pond's edge.
Apr 4, 2020 near Lee, MA
Misty marsh.
Apr 4, 2020 near Stockbr…, MA
The ruins of an old stone building.
Apr 4, 2020 near Lee, MA
This chimney stands as monument to the C.C.C. Camp that was once here.
Apr 4, 2020 near Stockbr…, MA
Hemlock Varnish Shelf (Ganoderma tsugae).
Apr 10, 2020 near Lee, MA
The stone chasm, remnants of the CCC camp.
Apr 10, 2020 near Stockbr…, MA
Mount Hunger at Konkapot Ridge.
Nov 7, 2024 near Otis, MA

Monterey Running

  • 47 Miles 75 Kilometers of Trail
  • 0 Recommended Routes
  • 12 Easy Trails Easy Trails
  • 12 Intermediate Trails Intermediate Trails
  • 1 Difficult Trail Difficult Trails
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