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Top Spots

Stevens Glen Trail

West Stockbridge, Massachusetts

1 mi / 249 ft gain

Olivia's Overlook Via Charcoal Trail

West Stockbridge, Massachusetts

1.74 mi / 489 ft gain

Burbank Trail

Richmond, Massachusetts

2.98 mi / 482 ft gain

Trail of the Ledges and Overbrook Trail

Lenox, Massachusetts

2.56 mi / 879 ft gain

Shaker Mountain Loop via Shaker Trail

Pittsfield, Massachusetts

5.19 mi / 1027 ft gain

Shaker Mountain (Short Option)

Pittsfield, Massachusetts

3.17 mi / 774 ft gain

Holy Mount via Shaker Trail

Pittsfield, Massachusetts

6.64 mi / 1302 ft gain

Harvey Mountain and Pinnacle Point Loop

Austerlitz, New York

4.33 mi / 748 ft gain

Harvey Mountain Trail

Austerlitz, New York

3.16 mi / 630 ft gain

Places to stay

Indian Hollow

Chesterfield, Massachusetts

Indian Hollow

Getaway Catskills East

Catskill, New York

Getaway Catskills East

From $209 / night

Getaway Catskills West

Catskill, New York

Getaway Catskills West

From $209 / night

Northampton / Springfield KOA Holiday

Westhampton, Massachusetts

Northampton / Springfield KOA Holiday

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

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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