Great Barrington
Top Spots
Flag Rock
Great Barrington, Massachusetts
3.49 mi
/ 663 ft gain
Flag Rock is an out-and-back trail that provides a good opportunity to view wildlife located near Great Barrington, Massachusetts.
Monument Mountain Summit
Great Barrington, Massachusetts
3.68 mi
/ 1001 ft gain
Monument Mountain Summit is an out-and-back trail where you may see beautiful wildflowers located near Great Barrington, Massachusetts.
East Mountain via Appalachian Trail
Great Barrington, Massachusetts
9.25 mi
/ 1857 ft gain
East Mountain via Appalachian Trail is an out-and-back trail where you may see beautiful wildflowers located near Great Barrington, Massachusetts.
Housie Rail Trail
Great Barrington, Massachusetts
8.56 mi
/ 233 ft gain
Housie Rail Trail is an out-and-back trail where you may see beautiful wildflowers located near Housatonic, Massachusetts.
Hickey and Squaw Loop
Great Barrington, Massachusetts
2.37 mi
/ 466 ft gain
Hickey and Squaw Loop is a loop trail where you may see beautiful wildflowers located near Stockbridge, Massachusetts.
Hike Monument Mountain
Great Barrington, Massachusetts
4.0
2 mi
/ 720 ft gain
At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under 3 miles round trip.Personally, I chose to take the Hickey Trail for the bulk of the elevation gain, ...
Hickey, Squaw and Indian Loop
Great Barrington, Massachusetts
2.7 mi
/ 587 ft gain
Hickey, Squaw and Indian Loop is a loop trail that provides a good opportunity to view wildlife located near Great Barrington, Massachusetts.
Appalachian Trail: Monterey to Sheffield
Sheffield, Massachusetts
7.19 mi
/ 1365 ft gain
Appalachian Trail: Monterey to Sheffield is a point-to-point trail where you may see beautiful wildflowers located near Sheffield, Massachusetts.
Mt. Wilcox and Beartown Mountain Trail Loop
Great Barrington, Massachusetts
9.29 mi
/ 981 ft gain
Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
Places to stay
Hillsdale, New York
Hillsdale Hideaway
Perched above the historic hamlet of Hillsdale, NY, enjoy your own private mountaintop with panoramic views of the Harlem Valley. Surroun...
From $125 / night
New Marlborough, Massachusetts
Echo Hill
This quiet, secluded camp on over 30 acres is a great place to unplug and rewind. There is also plenty to do in the towns nearby!
Echo H...
From $150 / night
The Lodge's Campsite
Picturesque camp in the middle of a forest. Enjoy the isolation and quiet at your tent, or experience all that the Berkshires and Taconi...
From $75 / night
Richmond, Massachusetts
Berkshire Mountain Hideaway
Magical, quiet campsite, only a short walk ( less than 1/4 mile) ) from easy access parking. Glacial rock to one direction, seasonal spri...
From $130 / night
MALOWINA FOREST
MALOWINA FOREST is a magical place of tranquility, wonder and breathtaking beauty where people deepen their love affair with nature and r...
From $200 / night
Ghent, New York
WATER + WOODS
This beautiful campsite is the perfect easy getaway whether you want to relax in the Adirondack chair on the edge of the pond on site, ma...
From $120 / night
Guides and stories
Quick links
- The best hiking trails in Great Barrington
- The best backpacking in Great Barrington
- The best camping in Great Barrington
- Top adventures in Great Barrington
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