9 days in Massachusetts Itinerary

9 days in Massachusetts Itinerary

Created using Inspirock Massachusetts sightseeing planner

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Make it your trip
Fly
1
Oak Bluffs, Martha's Vineyard
— 1 night
Ferry to 227 Clinton St., Falmouth, MA, Taxi to Sandwich
2
Sandwich
— 2 nights
Drive
3
Salem
— 2 nights
Drive
4
Shelburne Falls
— 1 night
Drive
5
Lenox
— 2 nights
Fly

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Oak Bluffs, Martha's Vineyard

— 1 night
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 24th (Sat): relax in the rural setting at Island Alpaca Company of Martha's Vineyard, then admire the landmark architecture of Trinity Park Tabernacle, and then take a stroll through Martha's Vineyard Camp meeting Association (MVCMA). Keep things going the next day: kick back and relax at Katama Beach/ South Beach, visit a coastal fixture at Edgartown Lighthouse, then relax in the rural setting at Morning Glory Farm, then don't miss a visit to Flying Horses Carousel, and finally walk around Ocean Park.

For where to stay, maps, traveler tips, and tourist information, you can read our Oak Bluffs online trip itinerary maker.

New York City to Oak Bluffs is an approximately 3-hour flight. You can also do a combination of car and ferry; or do a combination of train, bus, and ferry. Expect slightly colder temperatures when traveling from New York City in October; daily highs in Oak Bluffs reach 65°F and lows reach 46°F. Wrap up your sightseeing on the 25th (Sun) to allow time to travel to Sandwich.

Things to do in Oak Bluffs

Parks · Historic Sites · Neighborhoods · Beaches

Side Trip

Sandwich

— 2 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Start off your visit on the 26th (Mon): immerse yourself in nature at National Monument to the Forefathers, then make a trip to Old King's Hwy, then engage your brain at Sandwich Glass Museum, and finally take in the waterfront at Boardwalk. Get ready for a full day of sightseeing on the 27th (Tue): tour the pleasant surroundings at Shining Sea Bikeway, visit a coastal fixture at Nobska Point Lighthouse, explore the activities along Cape Cod Canal, then steep yourself in history at Hoxie House, and finally appreciate the history behind John F. Kennedy Memorial.

You can plan Sandwich trip in no time by asking Inspirock to help create your itinerary.

Getting from Oak Bluffs to Sandwich by combination of ferry and taxi takes about 1.5 hours. Other options: do a combination of ferry and bus. October in Sandwich sees daily highs of 64°F and lows of 46°F at night. Finish your sightseeing early on the 27th (Tue) to allow enough time to drive to Salem.

Things to do in Sandwich

Parks · Trails · Outdoors · Museums

Side Trips

Salem

— 2 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.
Start off your visit on the 28th (Wed): admire the striking features of Sargent House Museum, then get great views at Bearskin Neck, then take a memorable tour with Tours, and finally take in the waterfront at Pickering Wharf. On the next day, steep yourself in history at Salem Maritime National Historic Site, then admire the masterpieces at Count Orlok's Nightmare Gallery, then see the interesting displays at Gallows Hill Museum/Theatre, and finally look for gifts at Crow Haven Corner.

To find traveler tips, where to stay, reviews, and more tourist information, use the Salem trip itinerary maker site.

Drive from Sandwich to Salem in 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 64°F in October, and nighttime lows around 45°F. Wrap up your sightseeing on the 29th (Thu) early enough to travel to Shelburne Falls.

Things to do in Salem

Museums · Historic Sites · Shopping · Tours

Side Trips

Shelburne Falls

— 1 night
Shelburne Falls is a historic village in the towns of Shelburne and Buckland in Franklin County, Massachusetts, United States. On the 30th (Fri), see the interesting displays at Yankee Candle Flagship Store, then snap pictures at Bridge of Flowers, and then kick your exploration up a notch at some of the top local zipline courses and adventure parks.

To find other places to visit, more things to do, ratings, and other tourist information, go to the Shelburne Falls online attractions planner.

Traveling by car from Salem to Shelburne Falls takes 2.5 hours. In October, daytime highs in Shelburne Falls are 62°F, while nighttime lows are 41°F. Finish your sightseeing early on the 30th (Fri) so you can drive to Lenox.

Things to do in Shelburne Falls

Museums · Shopping · Tours · Adventure

Side Trips

Lenox

— 2 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. On the 31st (Sat), get engrossed in the history at The Mount, Edith Wharton's Home, get engrossed in the history at Hancock Shaker Village, and then take your sightseeing to a higher altitude at Monument Mountain. Here are some ideas for day two: take in the awesome beauty at Mount Greylock, explore the world behind art at MASS MoCA, and then take in the spiritual surroundings of National Shrine of the Divine Mercy.

Plan my trip to Lenox with suggested itineraries provided by Inspirock.

You can drive from Shelburne Falls to Lenox in 1.5 hours. Expect a daytime high around 60°F in October, and nighttime lows around 40°F. Wrap up your sightseeing on the 1st (Sun) to allow time to fly back home.

Things to do in Lenox

Museums · Historic Sites · Nature · Parks

Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
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.