33 days in Cambridge, Western Massachusetts & Boston Itinerary

33 days in Cambridge, Western Massachusetts & Boston Itinerary

Created using Inspirock Massachusetts trip itinerary planner
Make it your trip
Fly
1
Cambridge
— 6 nights
Drive
2
Brimfield
— 5 nights
Drive
3
Lenox
— 3 nights
Drive
4
Deerfield
— 3 nights
Drive
5
Boston
— 15 nights
Fly

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Cambridge — 6 nights

Best known as the location of two internationally renowned universities, Cambridge sits just across the Charles River from Boston.
Venture out of the city with trips to Concord (Ralph Waldo Emerson House, Louisa May Alcott's Orchard House, &more), Salem (Salem Witch Trials Memorial, Old Burying Point Cemetery, &more) and Springbrook Farm (in Littleton). There's much more to do: stroll the grounds of Mount Auburn Cemetery, deepen your understanding at Massachusetts Institute of Technology (MIT), tour the pleasant surroundings at Cambridge Common, and get to know the fascinating history of Lexington Visitors Center.

Start your trip to Cambridge by creating a personalized itinerary on Inspirock.

London, UK to Cambridge is an approximately 10.5-hour flight. Traveling from London to Cambridge, you'll gain 5 hours due to the time zone difference. October in Cambridge sees daily highs of 20°C and lows of 11°C at night. Finish your sightseeing early on the 10th (Sun) to allow enough time to travel to Brimfield.
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Historic Sites · Parks · Museums · Nature
Side Trips

Brimfield — 5 nights

Brimfield is a town in Hampden County, Massachusetts, United States. Get out of town with these interesting Brimfield side-trips: Saint Joseph's Abbey (in Spencer), Brookfield Orchards (in North Brookfield) and Barre Falls Dam (in Barre). And it doesn't end there: browse the exhibits of Old Sturbridge Village, take your sightseeing to a higher altitude at Peaked Mountain, experience rural life at Breezelands Orchards, and stroll through Airline North State Park Trail.

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Getting from Cambridge to Brimfield by car takes about 1.5 hours. Plan for little chillier nights when traveling from Cambridge in October since evenings lows in Brimfield dip to 5°C. Finish your sightseeing early on the 15th (Fri) to allow enough time to travel to Lenox.
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Parks · Historic Sites · Nature · Museums
Side Trips

Lenox — 3 nights

Lenox is an affluent town in Berkshire County, Massachusetts, United States. Change things up with these side-trips from Lenox: Vernon Rails-to-Trails (in Vernon), The Clark Art Institute (in Williamstown) and Ashuwillticook Rail Trail (in Adams). The adventure continues: admire the masterpieces at Norman Rockwell Museum, see the interesting displays at Polish Center of Discovery and Learning, and get engrossed in the history at The Mount, Edith Wharton's Home.

To see more things to do, traveler tips, and other tourist information, read our Lenox trip itinerary builder site.

Traveling by car from Brimfield to Lenox takes 1.5 hours. While traveling from Brimfield, expect slightly colder days and about the same nights in Lenox, ranging from highs of 18°C to lows of 5°C. Wrap up your sightseeing on the 18th (Mon) early enough to drive to Deerfield.
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Museums · Trails · Parks · Outdoors
Side Trips

Deerfield — 3 nights

Deerfield is a town in Franklin County, Massachusetts, United States. Deerfield is known for museums and shopping. Your trip includes some of its best attractions: relax in the rural setting at Clarkdale Fruit Farms, get engrossed in the history at Frary House, steep yourself in history at Historic Deerfield, and take in the views from Bridge of Flowers.

To find traveler tips, more things to do, and more tourist information, read Deerfield online driving holiday planner.

Traveling by car from Lenox to Deerfield takes 1.5 hours. October in Deerfield sees daily highs of 19°C and lows of 5°C at night. Finish your sightseeing early on the 21st (Thu) so you can drive to Boston.
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Museums · Parks · Historic Sites · Wildlife
Side Trips

Boston — 15 nights

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Get out of town with these interesting Boston side-trips: Plymouth (Plimoth Pawtuxet & Plymouth Rock), Salem (Salem Maritime National Historic Site, The House of the Seven Gables, &more) and Stone Bridge Farm (in Acushnet). And it doesn't end there: get to know the fascinating history of Marginal Way Walkway, examine the collection at The Breakers, trek along Cliff Walk, and take an in-depth tour of John F. Kennedy Presidential Museum & Library.

To find more things to do, reviews, maps, and other tourist information, you can read our Boston trip planner.

You can drive from Deerfield to Boston in 2 hours. Traveling from Deerfield in October, plan for a bit warmer nights in Boston, with lows around 11°C. Finish up your sightseeing early on the 5th (Fri) so you can catch the flight back home.
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Museums · Historic Sites · Parks · Neighborhoods
Side Trips