Top Spots

Beartown Mountain to Laura's Tower

Lee, Massachusetts

4.05 mi / 981 ft gain

Hike to Laura's Tower and Ice Glen

Stockbridge, Massachusetts

2.58 mi / 600 ft gain

Mary V. Flynn Trail

Stockbridge, Massachusetts

1.29 mi / 138 ft gain

Ice Glen Trail

Stockbridge, Massachusetts

1.36 mi / 259 ft gain

October Mountain Loop

Lenox, Massachusetts

6.69 mi / 1401 ft gain

Upper Goose Pond via Appalachian Trail

Lee, Massachusetts

6.56 mi / 922 ft gain

Appalachian Trail: Pittsfield Road to Goose Pond

Lee, Massachusetts

10 mi / 1581 ft gain

Turkey and Airplane Trail

Great Barrington, Massachusetts

3.22 mi / 302 ft gain

Basin Pond Trail

Becket, Massachusetts

2.17 mi / 292 ft gain

Places to stay

Richmond, Massachusetts

Berkshire Mountain Hideaway

From $130 / night

The Lodge's Campsite

From $75 / night

Glamping in Hephzibah

From $120 / night

New Marlborough, Massachusetts

Echo Hill

From $150 / night

Hillsdale, New York

Hillsdale Hideaway

From $125 / night

Lanesborough, Massachusetts

Birch Berry Pines

From $100 / night

Guides and stories

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

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