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Top Spots

Appalachian Trail: Monterey to Sheffield

Sheffield, Massachusetts

7.19 mi / 1365 ft gain

Mount Everett - South Pinnacle

Sheffield, Massachusetts

1.82 mi / 1086 ft gain

East Mountain via Appalachian Trail

Great Barrington, Massachusetts

9.25 mi / 1857 ft gain

Hike to Race Brook Falls

Sheffield, Massachusetts

4.0
3.4 mi / 1174 ft gain

Race Brook Trail to Mount Race

Sheffield, Massachusetts

5.51 mi / 1663 ft gain

Race Brook Falls and Mount Everett

Sheffield, Massachusetts

6.31 mi / 2156 ft gain

Bartholomew's Cobble Trail

Sheffield, Massachusetts

3.6 mi / 666 ft gain

Appalachian Trail from Jug End to Bear Mountain

Egremont, Massachusetts

10.81 mi / 3074 ft gain

Hike Mount Everett

Mount Washington, Massachusetts

4.6 mi

Places to stay

Echo Hill

New Marlborough, Massachusetts

Echo Hill

From $150 / night

Hillsdale Hideaway

Hillsdale, New York

Hillsdale Hideaway

From $125 / night

MALOWINA FOREST

MALOWINA FOREST

From $200 / night

Driftways Farm

Millerton, New York

Driftways Farm

From $125 / night

Hudson Valley Hilltop 1

Pine Plains, New York

Hudson Valley Hilltop 1

From $169 / night

Hudson Valley Hilltop 2

Pine Plains, New York

Hudson Valley Hilltop 2

From $169 / night

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

Pursuit Gear Kit 2018

Pursuit Gear Kit 2018

Pursuit Series

Trading the Metro for the Mountains: Pursuit New York 2018

Trading the Metro for the Mountains: Pursuit New York 2018

Emily Hlaváč Green

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