15 days in Western Massachusetts Itinerary

15 days in Western Massachusetts Itinerary

Created using Inspirock Western Massachusetts trip planner

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Route & dates

15 days in Western Massachusetts Itinerary

Start: Hartford
Drive:  45​min
1
Agawam
— 1 night
Drive:  1​h 15​min
2
South Deerfield
— 5 nights
Drive:  1​h 30​min
3
Williamstown
— 4 nights
Drive:  1​h 15​min
4
Stockbridge
— 4 nights
Drive:  1​h 30​min
End: Hartford

1
night
Agawam

Agawam ©
Agawam is a city in Hampden County, Massachusetts, United States. Start off your visit on the 17th (Fri): have fun and explore at Springfield Museums, pause for some photo ops at Dr. Seuss National Memorial Sculpture Garden, and then stroll through Stanley park. Get ready for a full day of sightseeing on the next day: browse the exhibits of Springfield Armory National Historic Site, examine the collection at Basketball Hall of Fame, and then find something for the whole family at Six Flags New England.

For more things to do, where to stay, traveler tips, and tourist information, you can read our Agawam online trip itinerary builder .

Hartford to Agawam is an approximately half hour car ride. In May, plan for daily highs up to 72°F, and evening lows to 48°F. Finish up your sightseeing early on the 18th (Sat) so you can travel to South Deerfield.

Things to do in Agawam

Museums Childrens Museums Theme Parks

Side Trips

Springfield, Stanley park
Highlights from your plan
Basketball Hall of Fame ©
Basketball Hall of Fame
Six Flags New England ©
Six Flags New England
Stanley park ©
Stanley park

5
nights
South Deerfield

South Deerfield ©
South Deerfield is a census-designated place (CDP) in Deerfield, Franklin County, Massachusetts, United States. Take a break from South Deerfield with a short trip to R. Michelson Galleries in Northampton, about 30 minutes away. And it doesn't end there: admire the natural beauty at Bridge of Flowers, contemplate the long history of Historic Deerfield, look for all kinds of wild species at Magic Wings Butterfly Conservatory and Gardens, and explore the galleries of Emily Dickinson Museum.

To find reviews, where to stay, ratings, and more tourist information, read South Deerfield road trip planning app .

You can drive from Agawam to South Deerfield in an hour. In May, plan for daily highs up to 70°F, and evening lows to 45°F. Wrap up your sightseeing on the 23rd (Thu) to allow time to travel to Williamstown.

Things to do in South Deerfield

Museums Parks Historic Sites

Side Trips

Northampton, Amherst, Deerfield, Shelburne Falls, Poet's Seat Tower
Highlights from your plan
Emily Dickinson Museum ©
Emily Dickinson Museum
Mount Sugarloaf State Reservation ©
Mount Sugarloaf State Reservation

4
nights
Williamstown

Williamstown ©
Williamstown is a town in Berkshire County, in the northwest corner of Massachusetts, United States. Step out of Williamstown with an excursion to Zipline in Charlemont--about 42 minutes away. Next up on the itinerary: admire the masterpieces at The Clark Art Institute, take a peaceful walk through Hopkin's Memorial Forest, get lost in a book at Chapin Library of Rare Books and Manuscripts, and identify plant and animal life at Mount Greylock State Reservation.

For ratings, other places to visit, and other tourist information, go to the Williamstown online tour itinerary planner .

You can drive from South Deerfield to Williamstown in 1.5 hours. In May, daily temperatures in Williamstown can reach 69°F, while at night they dip to 45°F. Finish your sightseeing early on the 27th (Mon) to allow enough time to travel to Stockbridge.

Things to do in Williamstown

Parks Outdoors Nature

Side Trips

Adams, North Adams, Zipline, Mount Greylock State Reservation
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Zipline
Williams College Museum of Art ©
Williams College Museum of Art

4
nights
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Step out of Stockbridge with an excursion to Crane Museum of Papermaking in Dalton--about 32 minutes away. There's much more to do: explore the world behind art at Norman Rockwell Museum, view the masterpieces at Schantz Galleries, take in nature's colorful creations at Naumkeag, and experience rural life at Hancock Shaker Village.

To see other places to visit, maps, more things to do, and more tourist information, read Stockbridge trip itinerary planner.

Traveling by car from Williamstown to Stockbridge takes an hour. May in Stockbridge sees daily highs of 68°F and lows of 45°F at night. Wrap up your sightseeing on the 31st (Fri) to allow time to drive back home.

Things to do in Stockbridge

Museums Historic Sites Parks

Side Trips

Lee, Pittsfield, Great Barrington, Crane Museum of Papermaking, Bidwell House Museum
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Naumkeag ©
Naumkeag
National Shrine of the Divine Mercy ©