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Top Spots

Beartown Mountain to Laura's Tower

Lee, Massachusetts

4.05 mi / 981 ft gain

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

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

Finerty Pond via Appalachian Trail

Lee, Massachusetts

5.97 mi / 1253 ft gain

Places to stay

Indian Hollow

Chesterfield, Massachusetts

Indian Hollow

Northampton / Springfield KOA Holiday

Westhampton, Massachusetts

Northampton / Springfield KOA Holiday

Getaway Catskills East

Catskill, New York

Getaway Catskills East

From $209 / night

Getaway Catskills West

Catskill, New York

Getaway Catskills West

From $209 / night

Northfield Brook Lake Group Shelters

Thomaston, Connecticut

Northfield Brook Lake Group Shelters

Guides and stories

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

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