32 days in Berkshires Itinerary

32 days in Berkshires Itinerary

Created using Inspirock Berkshires trip maker

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Route & dates

32 days in Berkshires Itinerary

Start: Newark
Drive:  3​h 30​min
Great Barrington
— 16 nights
Drive:  1​h 15​min
— 15 nights
Drive:  4​h 15​min
End: Newark

Great Barrington

Great Barrington ©
Great Barrington is a town in Berkshire County, Massachusetts, United States. Family-friendly places like Ski Butternut and Pleasant Valley Sanctuary will thrill your kids. Get out of town with these interesting Great Barrington side-trips: West Stockbridge (Turn Park Art Space & Olivia's Overlook), Lenox (Kennedy Park, First Lenox Library, & more) and Lee (Congregational Church, Lee Library, & more). And it doesn't end there: admire the masterpieces at Norman Rockwell Museum, examine the collection at Bidwell House Museum, stroll through Catamount Ski Area, and contemplate in the serene atmosphere at National Shrine of the Divine Mercy.

To see reviews, other places to visit, maps, and other tourist information, you can read our Great Barrington travel planner .

Newark to Great Barrington is an approximately 3-hour car ride. Plan for slightly colder temperatures traveling from Newark in April, with highs in Great Barrington at 54°F and lows at 33°F. Wrap up your sightseeing on the 8th (Wed) early enough to drive to Williamstown.

Things to do in Great Barrington

Parks Outdoors Nature

Side Trips

Lenox, Stockbridge, Lee, Pittsfield, Sheffield
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Ski Butternut ©
Ski Butternut
Bousquet Mountain ©
Bousquet Mountain


Williamstown ©
Williamstown is a town in Berkshire County, in the northwest corner of Massachusetts, United States. Bring the kids along to Zipline and Ioka Valley Farm. Change things up with these side-trips from Williamstown: Pittsfield (Hancock Shaker Village, Lake Onota, & more), Crane Museum of Papermaking (in Dalton) and Charlemont (Bissell Covered Bridge, Hail to the Sunrise / Mohawk Park, & more). There's much more to do: explore the world behind art at The Clark Art Institute, glide through natural beauty at Notchview, grab your bike and head to Village Bike Rentals, and browse the collection at Chapin Library of Rare Books and Manuscripts.

For other places to visit, ratings, maps, and more tourist information, refer to the Williamstown online vacation planner .

Traveling by car from Great Barrington to Williamstown takes 1.5 hours. In May, daytime highs in Williamstown are 69°F, while nighttime lows are 45°F. Finish your sightseeing early on the 23rd (Thu) to allow enough time to travel back home.

Things to do in Williamstown

Parks Nature Outdoors

Side Trips

North Adams, Charlemont, Pittsfield, Adams, Savoy
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Jiminy Peak Mountain Resort ©
Jiminy Peak Mountain Resort
Ioka Valley Farm ©
Ioka Valley Farm