Trips home
My trips
Favorites
Settings
Currency
$ U.S. Dollar
Language
english
Help
FAQ
3,078
trips planned today
4.6
out of 5
Trustscore rating
©

Berkshires trip planner

Create a fully customized day by day
itinerary for free

Itinerary planner

+ Add destination
—
2 adults
Adults
- +
Teens
- +
Kids
- +
Close
Trip Planner :  USA  /  Massachusetts  /  Berkshires

Berkshires

4.6
Art Museums · History Museums · Zipline
Plan the details of your Berkshires holiday and any onward adventuring with our easy-to-use United States journey builder tool.
Create a full itinerary — for free!

    Plan your trip to Berkshires

    • Get a personalized trip
      A full day by day itinerary based on your preferences
    • Customize it
      Refine your trip. We'll find the
      best routes and schedules
    • Book it
      Choose from the best hotels and activities. Up to 50% off
    • Manage it
      Everything in one place. Everyone on the same page.
    Know more

    Places to visit in Berkshires

    WilliamstownTrip planner Best for: Art Museum, Theater, Gift & Specialty Shop LenoxTrip planner Best for: Symphony, History Museum, Architectural Building CharlemontTrip planner Best for: Zipline, River Rafting / Tubing, Ski Area PittsfieldTrip planner Best for: History Museum, Theater, Specialty Museum AdamsTrip planner Best for: Mountain, Hiking Trail, Biking Trail

    Visit a single location or make it a multi-destination trip.

    Popular things to do in Berkshires

    See all ›
    The Clark Art Institute ©
    Art Museum
    The Clark Art Institute
    Williamstown
    4.8
    Duration: 2 hours
    ©
    Zipline
    Zipline
    Charlemont
    4.8
    Duration: 2h 30 min
    The Mount, Edith Wharton's Home ©
    History Museum
    The Mount, Edith Wharton's Home
    Lenox
    4.7
    Duration: 2 hours
    MASS MoCA ©
    Art Museum
    MASS MoCA
    North Adams
    4.6
    Duration: 2 hours

    Museums in Berkshires

    See all ›
    Hancock Shaker Village ©
    History Museum
    Hancock Shaker Village
    Pittsfield
    4.5
    Duration: 2 hours
    Norman Rockwell Museum ©
    Art Museum
    Norman Rockwell Museum
    Stockbridge
    4.8
    Duration: 2 hours
    Williams College Museum of Art ©
    Art Museum
    Williams College Museum of Art
    Williamstown
    4.6
    Duration: 2 hours
    Frelinghuysen Morris House & Studio ©
    Specialty Museum
    Frelinghuysen Morris House & Studio
    Lenox
    4.3
    Duration: 2 hours

    Nature in Berkshires

    See all ›
    Mount Greylock State Reservation ©
    State Park
    Mount Greylock State Reservation
    Lanesborough
    4.8
    Duration: 2 hours
    Monument Mountain ©
    Mountain
    Monument Mountain
    Great Barrington
    4.7
    Duration: 2 hours
    Mount Greylock ©
    Mountain
    Mount Greylock
    Adams
    4.8
    Duration: 2 hours
    Natural Bridge State Park ©
    State Park
    Natural Bridge State Park
    North Adams
    4.5
    Duration: 2 hours

    Hidden gems in Berkshires

    Bidwell House Museum ©
    Specialty Museum
    Bidwell House Museum
    Monterey
    4.9
    Duration: 1h 30 min
    Ashuwillticook Rail Trail ©
    Hiking Trail
    Ashuwillticook Rail Trail
    Adams
    4.7
    Duration: 2 hours
    Pleasant Valley Sanctuary
    Nature / Park
    Pleasant Valley Sanctuary
    Lenox
    4.8
    Duration: 2 hours
    Village Bike Rentals ©
    Biking Trail
    Village Bike Rentals
    Adams
    5.0
    Duration: 2 hours

    Parks in Berkshires

    Naumkeag ©
    Garden
    Naumkeag
    Stockbridge
    4.5
    Duration: 2 hours
    Bartholomew's Cobble Reservation ©
    Nature / Park
    Bartholomew's Cobble Reservation
    Sheffield
    4.7
    Duration: 2 hours
    Kennedy Park ©
    Park
    Kennedy Park
    Lenox
    4.5
    Duration: 2 hours
    Tyringham Cobble ©
    Park
    Tyringham Cobble
    Tyringham
    4.7
    Duration: 2 hours

    Shopping in Berkshires

    See all ›
    Guido's Fresh Marketplace ©
    Gift & Specialty Shop
    Guido's Fresh Marketplace
    Pittsfield
    4.4
    Duration: 2 hours
    Lee Premium Outlets ©
    Factory Outlet
    Lee Premium Outlets
    Lee
    3.8
    Duration: 2 hours
    A.L. Avery & Son General Store ©
    Gift & Specialty Shop
    A.L. Avery & Son General Store
    Charlemont
    4.9
    Duration: 2 hours
    Where'd You Get That!?, Inc. ©
    Gift & Specialty Shop
    Where'd You Get That!?, Inc.
    Williamstown
    4.8
    Duration: 2 hours

    Don't Miss a Thing.
    See & Do More.

    Where to stay in Berkshires

    Norman Rockwell Museum ©
    Browse hotels, guesthouses, and unique homes and book your stay on the world's leading accommodation sites.
    20 million rooms are at your fingertips!
    —
    2 adults
    Adults (12 +)
    - +
    Children (2-11)
    - +
    Infants (Under 2)
    - +
    Close

    Recently planned trips to Berkshires

    1 day in Lenox BY A USER FROM UNITED STATES The Mount, Edith Wharton's Home Ventfort Hall Mansion and Gilded Age Museum Tom Fiorini Sculpture Yard 26 days in United States, Toronto & Playa del Carmen BY A USER FROM ISRAEL Toronto Lake Placid North Adams 1 day in United States BY A USER FROM AUSTRALIA Boston Bar Harbor North Conway 12 days in Western Massachusetts BY A USER FROM UNITED STATES Pittsfield Springfield 2 days in Clarksburg BY A USER FROM UNITED STATES Clarksburg State Park Tannery Falls Woodford State Park 7 days in Massachusetts BY A USER FROM UNITED STATES Lenox Boston Sandwich 23 days in East Coast of USA & Philadelphia BY A USER FROM PHILIPPINES New York City Philadelphia Washington DC 1 day in Pittsfield BY A USER FROM UNITED STATES Concepts of Art Lenox Judaica Rhythms Massage & Bodywork Lake Onota 1 day in Stockbridge BY A USER FROM UNITED STATES Furnace Brook Winery at Hilltop Orchards Flourish Market National Shrine of the Divine Mercy 1 day in Stockbridge BY A USER FROM UNITED STATES Stockbridge 29 days in Massachusetts BY A USER FROM FRANCE Gloucester Lenox Sandwich 2 days in North Adams BY A USER FROM UNITED STATES Williams College Museum of Art The Clark Art Institute Natural Bridge State Park
    See all trips
    See also: