9 days in Massachusetts Itinerary

9 days in Massachusetts Itinerary

Created using Inspirock Massachusetts itinerary planner
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Make it your trip
Fly
1
Lenox
— 2 nights
Drive
2
Chatham
— 1 night
Taxi to Harwich Port, Harwich, MA, Ferry to Nantucket
3
Nantucket
— 2 nights
Fly
4
Salem
— 3 nights
Fly

S M T W T F S
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Lenox — 2 nights

Lenox is an affluent town in Berkshire County, Massachusetts, United States. Visiting Mount Greylock State Reservation and Monument Mountain will get you outdoors. Satisfy your inner culture vulture at Hancock Shaker Village and Yankee Candle Flagship Store. Venture out of the city with trips to MASS MoCA (in North Adams), Zipline (in Charlemont) and Mount Greylock (in Adams). The adventure continues: contemplate the long history of The Mount, Edith Wharton's Home.

To see reviews and tourist information, you can read our Lenox day trip site.

Minneapolis to Lenox is an approximately 4-hour flight. You can also drive; or do a combination of bus and train. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. In October, daily temperatures in Lenox can reach 60°F, while at night they dip to 40°F. Wrap up your sightseeing on the 19th (Wed) to allow time to drive to Chatham.
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Museums · Parks · Nature · Historic Sites
Side Trips
Find places to stay Oct 17 — 19:

Chatham — 1 night

Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Kick off your visit on the 20th (Thu): take an in-depth tour of Atwood Museum, steep yourself in history at Marconi-RCA Wireless Museum, then enjoy the sand and surf at Nauset Beach, and finally enjoy the sand and surf at Chatham Lighthouse Beach.

To see traveler tips, where to stay, more things to do, and tourist information, you can read our Chatham trip builder app.

Getting from Lenox to Chatham by car takes about 4 hours. Other options: take a bus; or do a combination of bus, train, and taxi. Traveling from Lenox in October, Chatham is somewhat warmer at night with lows of 50°F. Wrap up your sightseeing on the 20th (Thu) to allow time to travel to Nantucket.
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Beaches · Parks · Outdoors · Historic Sites
Side Trip
Find places to stay Oct 19 — 20:

Nantucket — 2 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. On the 21st (Fri), enjoy the sea views from Great Point Light, then visit a coastal fixture at Sankaty Head Lighthouse, and then kick back and relax at Siasconset Beach. Get ready for a full day of sightseeing on the 22nd (Sat): see the interesting displays at Whaling Museum, enjoy the sea views from Brant Point Lighthouse, and then kick back and relax at Madaket Beach.

Plan a Nantucket trip in moments using our itinerary builder.

You can do a combination of taxi and ferry from Chatham to Nantucket in 2.5 hours. Alternatively, you can do a combination of bus and ferry. Expect a daytime high around 64°F in October, and nighttime lows around 51°F. Finish your sightseeing early on the 22nd (Sat) to allow enough time to fly to Salem.
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Historic Sites · Beaches · Parks · Outdoors
Find places to stay Oct 20 — 22:

Salem — 3 nights

Witch City

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Get some cultural insight at The House of the Seven Gables and Buckman Tavern. Escape the urban bustle at Dolphin & Whale Watching and Minute Man National Historical Park. Explore the numerous day-trip ideas around Salem: Old First Parish Burying Ground (in Rockport) and Concord (Louisa May Alcott's Orchard House & The Old North Bridge). There's much more to do: get engrossed in the history at Gallows Hill Museum/Theatre, take in the waterfront activity at Pickering Wharf, stop by Crow Haven Corner, and examine the collection at Count Orlok's Nightmare Gallery.

To see more things to do, ratings, maps, and more tourist information, you can read our Salem attractions site.

Traveling by flight from Nantucket to Salem takes 2.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, bus, and train. Traveling from Nantucket in October, Salem is slightly colder at night with lows of 45°F. Finish up your sightseeing early on the 25th (Tue) so you can catch the flight back home.
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Historic Sites · Museums · Tours · Outdoors
Side Trips
Find places to stay Oct 22 — 25:

Massachusetts travel guide

4.3
History Museums · Nightlife · Art Museums
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.
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