4 days in Berkshires Itinerary

4 days in Berkshires Itinerary

Created using Inspirock Berkshires attractions planner

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Route & dates

4 days in Berkshires Itinerary

Start: Boston
Drive:  4​h 15​min
Great Barrington
— 1 night
Drive:  1​h 15​min
— 2 nights
Drive:  4​h
End: Boston

Great Barrington

Great Barrington ©
Great Barrington is a town in Berkshire County, Massachusetts, United States. Start off your visit on the 24th (Fri): admire the masterpieces at Norman Rockwell Museum, contemplate the long history of The Mount, Edith Wharton's Home, and then view the masterpieces at Ozzie's Glass Gallery. On the 25th (Sat), you'll have a packed day of sightseeing: take in the awesome beauty at Monument Mountain, admire the natural beauty at Naumkeag, and then steep yourself in history at Hancock Shaker Village.

For traveler tips, other places to visit, reviews, and tourist information, read Great Barrington trip itinerary planner.

New York City to Great Barrington is an approximately 3-hour car ride. Traveling from New York City in May, you can expect nighttime temperatures to be little chillier in Great Barrington, with lows of 45°F. Finish up your sightseeing early on the 25th (Sat) so you can go by car to Williamstown.

Things to do in Great Barrington

Museums Parks Historic Sites

Side Trips

Stockbridge, The Mount, Edith Wharton's Home, Hancock Shaker Village, Ozzie's Glass Gallery
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. On the 26th (Sun), explore the world behind art at The Clark Art Institute, then admire the masterpieces at MASS MoCA, and then tour the pleasant surroundings at Jiminy Peak Mountain Resort. Get ready for a full day of sightseeing on the next day: take in the views from Bissell Covered Bridge and then whizz through the canopy at some of the top local zipline courses and adventure parks.

To see traveler tips, reviews, and more tourist information, use the Williamstown itinerary planner.

You can drive from Great Barrington to Williamstown in 1.5 hours. In May, plan for daily highs up to 69°F, and evening lows to 45°F. Wrap up your sightseeing on the 27th (Mon) to allow time to travel back home.

Things to do in Williamstown

Outdoors Tours Wildlife

Side Trips

Charlemont, Jiminy Peak Mountain Resort, MASS MoCA
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute