8 days in Berkshires Itinerary

8 days in Berkshires Itinerary

Created using Inspirock Berkshires travel planner

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Route & dates

8 days in Berkshires Itinerary

Start: New York City
Drive:  2​h 45​min
Great Barrington
— 3 nights
Drive:  1​h 15​min
— 4 nights
Drive:  3​h 30​min
End: New York City

Great Barrington

Great Barrington ©
Great Barrington is a town in Berkshire County, Massachusetts, United States. Explore the numerous day-trip ideas around Great Barrington: Pittsfield (Hancock Shaker Village, Balderdash Cellars, & more). There's lots more to do: admire the masterpieces at Norman Rockwell Museum, steep yourself in history at The Mount, Edith Wharton's Home, identify plant and animal life at Pleasant Valley Sanctuary, and see the interesting displays at Ventfort Hall Mansion and Gilded Age Museum.

For photos, other places to visit, maps, and other tourist information, you can read our Great Barrington day trip planning site .

New York City to Great Barrington is an approximately 3-hour car ride. Traveling from New York City in September, things will get a bit cooler in Great Barrington: highs are around 72°F and lows about 49°F. Wrap up your sightseeing on the 1st (Tue) to allow time to drive to Williamstown.

Things to do in Great Barrington

Historic Sites Parks Museums

Side Trips

Stockbridge, Pittsfield, Lenox, Congregational Church
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
The Mount, Edith Wharton's Home ©
The Mount, Edith Wharton's Home
Hancock Shaker Village ©
Hancock Shaker Village


Williamstown ©
Williamstown is a town in Berkshire County, in the northwest corner of Massachusetts, United States. You'll find plenty of places to visit near Williamstown: Berkshire Museum (in Pittsfield) and Zipline (in Charlemont). There's lots more to do: admire the masterpieces at The Clark Art Institute, admire the majestic nature at Mount Greylock State Reservation, hit the slopes at Jiminy Peak Mountain Resort, and stop by Where'd You Get That!?, Inc..

For ratings, maps, traveler tips, and more tourist information, read Williamstown road trip planning app .

Traveling by car from Great Barrington to Williamstown takes 1.5 hours. In October, daytime highs in Williamstown are 62°F, while nighttime lows are 41°F. Cap off your sightseeing on the 5th (Sat) early enough to travel back home.

Things to do in Williamstown

Parks Outdoors Nature

Side Trips

North Adams, Adams, Berkshire Museum, Jiminy Peak Mountain Resort, Mount Greylock State Reservation
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Williams College Museum of Art ©
Williams College Museum of Art