4 days in Berkshires Itinerary

4 days in Berkshires Itinerary

Created using Inspirock Berkshires trip planner

©
This plan was created by another user. Make it your plan

Route & dates

4 days in Berkshires Itinerary

Start: Boston
Drive:  2​h 30​min
1
Stockbridge
— 1 night
Drive:  1​h 15​min
2
Charlemont
— 2 nights
Drive:  2​h 30​min
End: Boston

1
night
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Kick off your visit on the 24th (Thu): explore the galleries of The Mount, Edith Wharton's Home and then admire the masterpieces at Norman Rockwell Museum. On the next day, take in nature's colorful creations at Naumkeag, then steep yourself in history at Hancock Shaker Village, then take advantage of the amenities at Jiminy Peak Mountain Resort, and finally do a tasting at Balderdash Cellars.

To see photos, ratings, where to stay, and other tourist information, read our Stockbridge attractions planning app .

Boston to Stockbridge is an approximately 2.5-hour car ride. You can also take a bus; or take a train. Traveling from Boston in October, expect slightly colder with lows of 40°F in Stockbridge. Finish your sightseeing early on the 25th (Fri) to allow enough time to drive to Charlemont.

Things to do in Stockbridge

Museums Historic Sites Parks

Side Trips

Pittsfield, The Mount, Edith Wharton's Home, Jiminy Peak Mountain Resort
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Naumkeag ©
Naumkeag
The Mount, Edith Wharton's Home ©
The Mount, Edith Wharton's Home

2
nights
Charlemont

Charlemont is a town in Franklin County, Massachusetts, United States. Start off your visit on the 26th (Sat): admire the majestic nature at Mount Greylock State Reservation, explore the world behind art at The Clark Art Institute, and then admire the masterpieces at MASS MoCA. On the 27th (Sun), you'll have a packed day of sightseeing: immerse yourself in nature at Natural Bridge State Park and then whizz through the canopy at some of the top local zipline courses and adventure parks.

To see maps, other places to visit, photos, and more tourist information, you can read our Charlemont tour itinerary planner .

Traveling by car from Stockbridge to Charlemont takes 1.5 hours. In October, plan for daily highs up to 62°F, and evening lows to 41°F. Wrap up your sightseeing on the 27th (Sun) early enough to travel back home.

Things to do in Charlemont

Outdoors Tours Adventure

Side Trips

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