7 days in Berkshires Itinerary

7 days in Berkshires Itinerary

Created using Inspirock Berkshires vacation planner

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Make it your trip
Drive
1
Williamstown
— 2 nights
Drive
2
West Stockbridge
— 1 night
Drive
3
Stockbridge
— 3 nights
Drive

S M T W T F S
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Williamstown

— 2 nights
Williamstown is a town in Berkshire County, in the northwest corner of Massachusetts, United States. Get in touch with nature at Zipline and Mount Greylock State Reservation. Give yourself a bit of retail therapy at Where'd You Get That!?, Inc. and A.L. Avery & Son General Store. There's more to do: explore the world behind art at The Clark Art Institute and fly down the slopes at Jiminy Peak Mountain Resort.

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

Boston to Williamstown is an approximately 3-hour car ride. Traveling from Boston in November, expect slightly colder with lows of 29°F in Williamstown. Wrap up your sightseeing on the 8th (Thu) to allow time to travel to West Stockbridge.

Things to do in Williamstown

Outdoors · Parks · Adventure · Tours

Side Trips

West Stockbridge

— 1 night
West Stockbridge is a town in Berkshire County, Massachusetts, United States. On the 9th (Fri), stop by Charles H. Baldwin & Sons, immerse yourself in nature at October Mountain State Forest, then look for gifts at Museum Facsimiles Outlet Store, and finally delve into the lush surroundings at Pittsfield State Forest.

To find photos, maps, reviews, and more tourist information, go to the West Stockbridge itinerary maker tool.

Traveling by car from Williamstown to West Stockbridge takes an hour. In November, daily temperatures in West Stockbridge can reach 47°F, while at night they dip to 28°F. Wrap up your sightseeing on the 9th (Fri) to allow time to travel to Stockbridge.

Things to do in West Stockbridge

Parks · Nature · Shopping

Side Trips

Stockbridge

— 3 nights
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Escape the urban bustle at American Legion and Peoples State Forests and Lovers Leap State Park. Give yourself a bit of retail therapy at Williams & Sons Country Store and Sharon Audubon Center. You'll find plenty of places to visit near Stockbridge: Millbrook Vineyards & Winery (in Millbrook), Hunter Mountain (in Hunter) and Franklin D. Roosevelt Presidential Library and Museum (in Hyde Park). There's more to do: look for gifts at Guido's Fresh Marketplace.

To see reviews, other places to visit, ratings, and more tourist information, go to the Stockbridge trip itinerary planning tool.

Stockbridge is just a short distance from West Stockbridge. In November, daily temperatures in Stockbridge can reach 47°F, while at night they dip to 28°F. Finish up your sightseeing early on the 12th (Mon) so you can go by car back home.

Things to do in Stockbridge

Parks · Outdoors · Nature · Winter Sports

Side Trips

Berkshires travel guide

4.6
Art Museums · Historic Sites · Zipline