60 days in Western Massachusetts Itinerary

60 days in Western Massachusetts Itinerary

Created using Inspirock Western Massachusetts attractions planner

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Route & dates

60 days in Western Massachusetts Itinerary

Start: Boston
Drive:  1​h 45​min
— 18 nights
Drive:  1​h 45​min
— 21 nights
Drive:  1​h 30​min
— 20 nights
Drive:  3​h
End: Boston


Springfield ©
Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Visit Emily Dickinson Museum and Historic Northampton for their historical value. Let the collections at Basketball Hall of Fame and Springfield Museums capture your imagination. Venture out of the city with trips to Amherst (Mt. Pollux, Amherst Public Library, & more), Northampton (Smith College, Look Memorial Park, & more) and Hadley (Silvio O. Conte National Fish and Wildlife Refuge, Summit House, & more). The adventure continues: identify plant and animal life at Mount Tom State Reservation, explore the world behind art at Eric Carle Museum of Picture Book Art, get in on the family fun at Six Flags New England, and take an in-depth tour of Polish Center of Discovery and Learning.

For ratings, where to stay, more things to do, and more tourist information, you can read our Springfield online trip builder .

Boston to Springfield is an approximately 2-hour car ride. You can also take a bus; or take a train. Traveling from Boston in September, expect a bit cooler with lows of 51°F in Springfield. Finish your sightseeing early on the 19th (Thu) so you can travel to Pittsfield.

Things to do in Springfield

Parks Museums Nature

Side Trips

Amherst, Northampton, Holyoke, Hadley, South Hadley
Highlights from your plan
Mount Tom State Reservation ©
Mount Tom State Reservation
Springfield Museums ©
Springfield Museums
Basketball Hall of Fame ©
Basketball Hall of Fame


Pittsfield ©
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Your cultural itinerary includes sights like Norman Rockwell Museum and The Mount, Edith Wharton's Home. Museum-lovers will appreciate The Clark Art Institute and Hancock Shaker Village. Get out of town with these interesting Pittsfield side-trips: Chesterwood Museum (in Stockbridge), Monterey (Bidwell House Museum & Beartown State Forest) and Williamstown (Williams College Museum of Art, Chapin Library of Rare Books and Manuscripts, & more). The adventure continues: immerse yourself in nature at Mount Greylock State Reservation, identify plant and animal life at Goose Pond Reservation, examine the collection at Berkshire Museum, and contemplate in the serene atmosphere at National Shrine of the Divine Mercy.

To see photos, other places to visit, where to stay, and tourist information, read Pittsfield trip planner.

Traveling by car from Springfield to Pittsfield takes 1.5 hours. When traveling from Springfield in September, plan for a bit cooler days and about the same nights in Pittsfield: temperatures range from 72°F by day to 49°F at night. Wrap up your sightseeing on the 10th (Thu) early enough to travel to Deerfield.

Things to do in Pittsfield

Parks Nature Outdoors

Side Trips

Lenox, Stockbridge, North Adams, Lee, Adams
Highlights from your plan
Hancock Shaker Village ©
Hancock Shaker Village
Norman Rockwell Museum ©
Norman Rockwell Museum
The Clark Art Institute ©
The Clark Art Institute


Deerfield ©
Deerfield is a town in Franklin County, Massachusetts, United States. Historic Deerfield and Frary House will appeal to history buffs. Your cultural itinerary includes sights like Great Falls Discovery Center and Montague Bookmill. Explore the numerous day-trip ideas around Deerfield: Northfield Mountain Recreation and Environmental Center (in Northfield), Charlemont (Bissell Covered Bridge, Zipline, & more) and Gould's Sugar House (in Shelburne Falls). There's lots more to do: look for all kinds of wild species at Mount Sugarloaf State Reservation, get engrossed in the history at Memorial Hall Museum, admire the natural beauty at Magic Wings Butterfly Conservatory and Gardens, and head outdoors with Crumpin-Fox Club.

To find out how to plan a trip to Deerfield, use our trip itinerary maker.

You can drive from Pittsfield to Deerfield in 1.5 hours. In October, daily temperatures in Deerfield can reach 62°F, while at night they dip to 40°F. On the 30th (Wed), you'll travel back home.

Things to do in Deerfield

Parks Nature Outdoors

Side Trips

Shelburne Falls, Greenfield, Charlemont, Turners Falls, South Deerfield
Highlights from your plan
Historic Deerfield ©
Historic Deerfield
Memorial Hall Museum ©
Memorial Hall Museum