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  • Great Barrington
  • Great Barrington

    Top Spots

    Flag Rock

    Great Barrington, Massachusetts

    3.49 mi / 663 ft gain

    Monument Mountain Summit

    Great Barrington, Massachusetts

    3.68 mi / 1001 ft gain

    East Mountain via Appalachian Trail

    Great Barrington, Massachusetts

    9.25 mi / 1857 ft gain

    Housie Rail Trail

    Great Barrington, Massachusetts

    8.56 mi / 233 ft gain

    Hickey and Squaw Loop

    Great Barrington, Massachusetts

    2.37 mi / 466 ft gain

    Hike Monument Mountain

    Great Barrington, Massachusetts

    4.0
    2 mi / 720 ft gain

    Hickey, Squaw and Indian Loop

    Great Barrington, Massachusetts

    2.7 mi / 587 ft gain

    Appalachian Trail: Monterey to Sheffield

    Sheffield, Massachusetts

    7.19 mi / 1365 ft gain

    Mt. Wilcox and Beartown Mountain Trail Loop

    Great Barrington, Massachusetts

    9.29 mi / 981 ft gain

    Places to stay

    Getaway Catskills West

    Catskill, New York

    Getaway Catskills West

    From $209 / night

    Getaway Catskills East

    Catskill, New York

    Getaway Catskills East

    From $209 / night

    Indian Hollow

    Chesterfield, Massachusetts

    Indian Hollow

    Northampton / Springfield KOA Holiday

    Westhampton, Massachusetts

    Northampton / Springfield KOA Holiday

    Northfield Brook Lake Group Shelters

    Thomaston, Connecticut

    Northfield Brook Lake Group Shelters

    Hop Brook Lake Recreation Area

    Naugatuck, Connecticut

    Hop Brook Lake Recreation Area

    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

    Quick links