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Top Spots

Appalachian Trail: Washington to Dalton

Washington, Massachusetts

17.51 mi / 2592 ft gain

Rudd Pond Loop Trail

Becket, Massachusetts

1.71 mi / 82 ft gain

Basin Pond Trail

Becket, Massachusetts

2.17 mi / 292 ft gain

Dorothy Frances Pink Trail Loop

Peru, Massachusetts

2.09 mi / 203 ft gain

Dorothy Frances Orange Trail Loop

Peru, Massachusetts

1.43 mi / 161 ft gain

Appalachian Trail: Lee to Tyringham

Lee, Massachusetts

8.68 mi / 1437 ft gain

Finerty Pond via Appalachian Trail

Lee, Massachusetts

5.97 mi / 1253 ft gain

Upper Goose Pond

Lee, Massachusetts

3.56 mi / 715 ft gain

Old Mill Trail

Hinsdale, Massachusetts

2.96 mi / 276 ft gain

Places to stay

Indian Hollow

Chesterfield, Massachusetts

Indian Hollow

Northampton / Springfield KOA Holiday

Westhampton, Massachusetts

Northampton / Springfield KOA Holiday

Getaway Catskills West

Catskill, New York

Getaway Catskills West

From $209 / night

Getaway Catskills East

Catskill, New York

Getaway Catskills East

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

The Outbound Collective

From NYC to the Slopes: A Weekend Ski Getaway

From NYC to the Slopes: A Weekend Ski Getaway

Sara Sheehy

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