8 days in Berkshires Itinerary

8 days in Berkshires Itinerary

Created using Inspirock Berkshires trip planner

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Route & dates

8 days in Berkshires Itinerary

Start: San Francisco
Fly + Drive:  15​h
1
Great Barrington
— 3 nights
Drive:  1​h 15​min
2
Williamstown
— 3 nights
Drive + Fly:  11​h 30​min
End: San Francisco

3
nights
Great Barrington

Great Barrington ©
Great Barrington is a town in Berkshire County, Massachusetts, United States. Museum-lovers will appreciate Norman Rockwell Museum and Bidwell House Museum. Escape the urban bustle at Pleasant Valley Sanctuary and Cranwell Resort Spa and Golf Club. Venture out of the city with trips to Pittsfield (Hancock Shaker Village, Balderdash Cellars, & more) and Richmond (Furnace Brook Winery at Hilltop Orchards & Balderdash Cellars). There's still lots to do: learn about winemaking at Les Trois Emme Winery, examine the collection at Ventfort Hall Mansion and Gilded Age Museum, take in the spiritual surroundings of Congregational Church, and brush up on your knowledge of spirits at Berkshire Mountain Distillers.

For reviews, where to stay, maps, and tourist information, read Great Barrington trip site .

San Francisco to Great Barrington is an approximately 15-hour flight. You can also drive. The time zone difference moving from Pacific Standard Time to Eastern Standard Time is 3 hours. Plan for slightly colder temperatures traveling from San Francisco in October, with highs in Great Barrington at 60°F and lows at 40°F. Finish your sightseeing early on the 16th (Wed) so you can drive to Williamstown.

Things to do in Great Barrington

Museums Historic Sites Wineries

Side Trips

Lenox, Stockbridge, Pittsfield, Lee, Richmond
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

3
nights
Williamstown

Williamstown ©
Williamstown is a town in Berkshire County, in the northwest corner of Massachusetts, United States. Get outdoors at Zipline and Mount Greylock. Appreciate the collections at The Clark Art Institute and MASS MoCA. There's lots more to do: immerse yourself in nature at Mount Greylock State Reservation, indulge your thirst for a good beer at Bright Ideas Brewing, and stop by Sweet Brook Farm.

To find more things to do, maps, and more tourist information, read our Williamstown online trip itinerary builder .

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. On the 19th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Williamstown

Wildlife Parks Nature

Side Trips

North Adams, Zipline, Mount Greylock, Mount Greylock State Reservation
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Zipline
MASS MoCA ©
MASS MoCA