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

Hidden Hoosic Riverside Camp

From $150 / night

Overall Rustic

From $115 / night

Lanesborough, Massachusetts

Birch Berry Pines

From $100 / night

Stephentown, New York

Round Mountain Camp

From $100 / night

Cropseyville, New York

Camp MoonChild site 2

From $40 / night

Cropseyville, New York

Camp MoonChild site 1

From $40 / night

Guides and stories

From NYC to the Slopes: A Weekend Ski Getaway

Sara Sheehy

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

Quick links