5 days in Berkshires Itinerary

5 days in Berkshires Itinerary

Created using Inspirock Berkshires trip planner
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Make it your trip
Drive
1
Stockbridge
— 2 nights
Drive
2
Williamstown
— 2 nights
Drive

S M T W T F S
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Stockbridge — 2 nights

Stockbridge is a town in Berkshire County in western Massachusetts, United States. Escape the urban bustle at Herman Melville's Arrowhead and Concepts of Art Lenox Judaica. You'll explore the less-touristy side of things at Furnace Brook Winery at Hilltop Orchards and Guido's Fresh Marketplace. Step out of Stockbridge with an excursion to Crane Museum of Papermaking in Dalton--about 32 minutes away. Next up on the itinerary: take in the exciting artwork at Schantz Galleries Contemporary Glass, look for gifts at Charles H. Baldwin & Sons, play a few rounds at Cranwell Resort Spa and Golf Club, and look for all kinds of wild species at Goose Pond Reservation.

To see reviews, more things to do, maps, and more tourist information, read Stockbridge trip planner.

Newark to Stockbridge is an approximately 3-hour car ride. You can also do a combination of train and bus. In June, Stockbridge is little chillier than Newark - with highs of 74°F and lows of 53°F. Wrap up your sightseeing on the 7th (Tue) early enough to drive to Williamstown.
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Outdoors · Parks · Museums · Shopping
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Find places to stay Jun 5 — 7:

Williamstown — 2 nights

Williamstown is a town in Berkshire County, in the northwest corner of Massachusetts, United States. Kick off your visit on the 8th (Wed): admire the majestic nature at Mount Greylock State Reservation, then relax in the rural setting at Ioka Valley Farm, and then relax in the rural setting at Sweet Brook Farm. Get ready for a full day of sightseeing on the next day: hike along Ashuwillticook Rail Trail and then get all the equipment you need at Village Bike Rentals.

For traveler tips, reviews, and other tourist information, you can read our Williamstown route app.

Getting from Stockbridge to Williamstown by car takes about an hour. In June, daily temperatures in Williamstown can reach 76°F, while at night they dip to 54°F. Finish your sightseeing early on the 9th (Thu) to allow enough time to drive back home.
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Parks · Trails · Outdoors · Wildlife
Side Trips
Find places to stay Jun 7 — 9:

Berkshires travel guide

4.6
Art Museums · Historic Sites · Zipline