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Berkshires trip planner

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Trip Planner :  USA  /  Massachusetts  /  Berkshires

Berkshires

4.6
Art Museums · Historic Sites · Zipline
Plan the details of your Berkshires holiday and any onward adventuring with our easy-to-use United States journey builder tool.
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    Plan your trip to Berkshires

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    Places to visit in Berkshires

    LenoxTrip planner Best for: Symphony, Historic Site, Architectural Building WilliamstownTrip planner Best for: Art Museum, Theater, Gift & Specialty Shop Great BarringtonTrip planner Best for: Mountain, Ski Area, Hiking Trail HancockTrip planner Best for: Ski Area PittsfieldTrip planner Best for: Historic Site, Theater, Specialty Museum
    Visit a single location or make it a multi-destination trip.

    Popular things to do in Berkshires

    The Mount, Edith Wharton's Home ©
    Historic Site
    The Mount, Edith Wharton's Home
    Lenox
    4.7
    Duration: 2h 30 min
    The Clark Art Institute ©
    Art Museum
    The Clark Art Institute
    Williamstown
    4.8
    Duration: 2 hours
    Jiminy Peak Mountain Resort ©
    Ski Area
    Jiminy Peak Mountain Resort
    Hancock
    3.8
    Duration: 2 hours
    Ski Butternut ©
    Ski Area
    Ski Butternut
    Great Barrington
    4.1
    Duration: 2 hours

    Museums in Berkshires

    MASS MoCA ©
    Art Museum
    MASS MoCA
    North Adams
    4.6
    Duration: 2 hours
    Norman Rockwell Museum ©
    Art Museum
    Norman Rockwell Museum
    Stockbridge
    4.7
    Duration: 1h 30 min
    Williams College Museum of Art ©
    Art Museum
    Williams College Museum of Art
    Williamstown
    4.6
    Duration: 30 minutes
    Berkshire Museum ©
    Specialty Museum
    Berkshire Museum
    Pittsfield
    4.2
    Duration: 2 hours

    Nature in Berkshires

    Monument Mountain ©
    Mountain
    Monument Mountain
    Great Barrington
    4.7
    Duration: 2 hours
    Lenox Mountain
    Mountain
    Lenox Mountain
    Lenox
    5.0
    Duration: 2 hours
    Mount Greylock ©
    Mountain
    Mount Greylock
    Adams
    4.8
    Duration: 2 hours
    Mount Greylock State Reservation ©
    State Park
    Mount Greylock State Reservation
    Lanesborough
    4.8
    Duration: 2 hours

    Hidden gems in Berkshires

    Maple Corner Farm Cross Country Ski Area
    Cross-country Ski Area
    Maple Corner Farm Cross Country Ski Area
    Granville
    4.8
    Duration: 2 hours
    Ashuwillticook Rail Trail ©
    Hiking Trail
    Ashuwillticook Rail Trail
    Adams
    4.7
    Duration: 2 hours
    Berkshire Rivers Fly Fishing ©
    Fishing Charter / Tour
    Berkshire Rivers Fly Fishing
    Great Barrington
    5.0
    Duration: 2 hours
    Balderdash Cellars ©
    Winery / Vineyard
    Balderdash Cellars
    Richmond
    4.8
    Duration: 1h 30 min

    Historic Sites in Berkshires

    Hancock Shaker Village ©
    Historic Site
    Hancock Shaker Village
    Pittsfield
    4.5
    Duration: 2 hours
    National Shrine of the Divine Mercy ©
    Religious Site
    National Shrine of the Divine Mercy
    Stockbridge
    4.8
    Duration: 2 hours
    Congregational Church ©
    Religious Site
    Congregational Church
    Lee
    4.9
    Duration: 2 hours
    Birthplace of Susan B. Anthony ©
    Historic Site
    Birthplace of Susan B. Anthony
    Adams
    4.3
    Duration: 2 hours

    Shopping in Berkshires

    Flourish Market ©
    Antique Store
    Flourish Market
    West Stockbridge
    4.9
    Duration: 30 minutes
    A.L. Avery & Son General Store ©
    Gift & Specialty Shop
    A.L. Avery & Son General Store
    Charlemont
    4.9
    Duration: 2 hours
    Asia Barong ©
    Antique Store
    Asia Barong
    Great Barrington
    4.7
    Duration: 1h 30 min
    Where'd You Get That!?, Inc. ©
    Gift & Specialty Shop
    Where'd You Get That!?, Inc.
    Williamstown
    4.8
    Duration: 2 hours
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    Recently planned trips to Berkshires

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