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Top Spots

Laura's Tower and Ice Glen

Stockbridge, Massachusetts

5.0
2.4 mi / 676 ft gain

Mary V. Flynn Trail

Stockbridge, Massachusetts

1.29 mi / 138 ft gain

Bowkers Woods Lower Trail

Stockbridge, Massachusetts

0.95 mi / 144 ft gain

Beartown Mountain to Laura's Tower

Lee, Massachusetts

4.05 mi / 981 ft gain

Hickey, Squaw and Indian Loop

Great Barrington, Massachusetts

2.7 mi / 587 ft gain

Hike Monument Mountain

Great Barrington, Massachusetts

4.0
2 mi / 720 ft gain

Hickey and Squaw Loop

Great Barrington, Massachusetts

2.37 mi / 466 ft gain

Housie Rail Trail

Great Barrington, Massachusetts

8.56 mi / 233 ft gain

Monument Mountain Summit

Great Barrington, Massachusetts

3.68 mi / 1001 ft gain

Places to stay

Berkshire Mountain Hideaway

Richmond, Massachusetts

Berkshire Mountain Hideaway

From $130 / night

The Lodge's Campsite

The Lodge's Campsite

From $75 / night

Hillsdale Hideaway

Hillsdale, New York

Hillsdale Hideaway

From $125 / night

Echo Hill

New Marlborough, Massachusetts

Echo Hill

From $150 / night

WATER + WOODS

Ghent, New York

WATER + WOODS

From $120 / night

Glamping in Hephzibah

Glamping in Hephzibah

From $120 / night

Guides and stories

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

Pursuit Gear Kit 2018

Pursuit Gear Kit 2018

Pursuit Series

Trading the Metro for the Mountains: Pursuit New York 2018

Trading the Metro for the Mountains: Pursuit New York 2018

Emily Hlaváč Green

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