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Berkshires trip planner
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itinerary for free
Berkshires
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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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
Hidden gems in Berkshires
Parks in Berkshires
Where to stay in Berkshires

Browse hotels, guesthouses, and unique homes and book your stay on the world's leading accommodation sites.
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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