3 days in Western Massachusetts Itinerary

Created using Inspirock Western Massachusetts trip planner
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Make it your trip
Drive
1
Springfield
— 1 night
Drive
2
Pittsfield
— 1 night
Drive

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Springfield — 1 night

Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Kick off your visit on the 2nd (Fri): have fun and explore at Springfield Museums and then see the interesting displays at Yankee Candle Flagship Store. Get ready for a full day of sightseeing on the 3rd (Sat): see the interesting displays at Basketball Hall of Fame, then walk around Forest Park, then explore the activities along Watershops Pond, and finally cool off at Six Flags New England.

To find other places to visit, more things to do, photos, and more tourist information, read our Springfield trip itinerary planning tool.

Hartford to Springfield is an approximately half hour car ride. You can also take a bus; or take a train. Expect a daytime high around 40°F in December, and nighttime lows around 24°F. Cap off your sightseeing on the 3rd (Sat) early enough to go by car to Pittsfield.
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Museums · Childrens Museums · Parks · Shopping
Side Trips

Pittsfield — 1 night

Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Start off your visit on the 4th (Sun): take in nature's colorful creations at Naumkeag, then admire the masterpieces at Norman Rockwell Museum, then do a tasting at Balderdash Cellars, and finally hit the slopes at Jiminy Peak Mountain Resort.

To find reviews, traveler tips, other places to visit, and tourist information, go to the Pittsfield trip planner.

You can drive from Springfield to Pittsfield in 1.5 hours. In December, plan for daily highs up to 37°F, and evening lows to 23°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to drive back home.
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Parks · Winter Sports · Outdoors · Museums
Side Trips