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Williamstown

Top Spots

Pine Cobble Trail

Williamstown, Massachusetts

3.11 mi / 1201 ft gain

Chestnut Trail to the Class of '98 Trail to the Appalachian Trail

Williamstown, Massachusetts

3.27 mi / 1352 ft gain

Hopkins Memorial Forest Trail

Williamstown, Massachusetts

4.16 mi / 709 ft gain

Fitch Trail to RRR Brooks Trail

Williamstown, Massachusetts

4.32 mi / 1125 ft gain

RRR Brooks Trail to Shepherd's Well to Taconic Crest

Williamstown, Massachusetts

4.92 mi / 1030 ft gain

Mountain Meadow Preserve Trail

Pownal, Vermont

4.52 mi / 791 ft gain

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

North Adams, Massachusetts

4.51 mi / 1427 ft gain

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

North Adams, Massachusetts

13.37 mi / 4652 ft gain

Prospect Overlook via Appalachian Trail

North Adams, Massachusetts

3.7 mi / 1447 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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