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Top Spots

Natural Bridge Trail

North Adams, Massachusetts

0.33 mi / 112 ft gain

The Cascades Trail

North Adams, Massachusetts

1.97 mi / 315 ft gain

Mahican-Mohawk Trail

North Adams, Massachusetts

1.43 mi / 705 ft gain

Appalachian Trail: North Adams (Eph's Lookout) to Harmon Hill and Bennington

North Adams, Massachusetts

4.51 mi / 1427 ft gain

Bellows Pipe Trail to Ragged Mountain

North Adams, Massachusetts

4.52 mi / 942 ft gain

Bernard Farm Trail

North Adams, Massachusetts

3.53 mi / 1178 ft gain

Prospect Overlook via Appalachian Trail

North Adams, Massachusetts

3.7 mi / 1447 ft gain

Mount Prospect, Mount Williams, and Mount Greylock Loop via Appalachian Trail

North Adams, Massachusetts

13.37 mi / 4652 ft gain

Busby Trail to Spruce Hill Loop

Florida, Massachusetts

3.95 mi / 837 ft gain

Places to stay

Indian Hollow

Chesterfield, Massachusetts

Indian Hollow

Townshend Lake Day Use Area

Townshend, Vermont

Townshend Lake Day Use Area

Northampton / Springfield KOA Holiday

Westhampton, Massachusetts

Northampton / Springfield KOA Holiday

Winhall Brook

Londonderry, Vermont

Winhall Brook

Hapgood Pond

Peru, Vermont

Hapgood Pond

Guides and stories

From NYC to the Slopes: A Weekend Ski Getaway

From NYC to the Slopes: A Weekend Ski Getaway

Sara Sheehy

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

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