60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts itinerary maker

Make it your trip
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Boston
— 28 nights
Fly
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Provincetown
— 7 nights
Drive
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Sandwich
— 6 nights
Taxi to 227 Clinton St., Falmouth, MA, Ferry to Oak Bluffs
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Oak Bluffs, Martha's Vineyard
— 5 nights
Ferry
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Nantucket
— 7 nights
Ferry to Hyannis, MA, Drive to Lenox
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Lenox
— 6 nights
Drive

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Boston

— 28 nights

Beantown

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.
Change things up with these side-trips from Boston: Independence Park (in Beverly), Salem (Pickering Wharf, Salem Witch Museum, &more) and Codman Community Farms (in Lincoln). There's lots more to do: admire the natural beauty at Boston Public Garden, get engrossed in the history at Boston Tea Party Ships & Museum, explore the world behind art at Isabella Stewart Gardner Museum, and get to know the fascinating history of Freedom Trail.

To find maps, other places to visit, and other tourist information, go to the Boston journey planner.

Use the Route module to find suitable travel options from your home destination to Boston. In October, daytime highs in Boston are 64°F, while nighttime lows are 50°F. Wrap up your sightseeing on the 29th (Thu) to allow time to fly to Provincetown.

Things to do in Boston

Historic Sites · Museums · Parks · Shopping

Side Trips

Provincetown

— 7 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Venture out of the city with trips to Eastham (Nauset Light Beach, Salt Pond Visitor Center, &more) and Orleans (Nauset Inlet, Addison Art Gallery, &more). There's lots more to do: kick back and relax at Cape Cod National Seashore, tour the pleasant surroundings at Race Point Beach, appreciate the history behind Pilgrim Monument & Provincetown Museum, and browse the collection at Provincetown Library.

To find maps, more things to do, other places to visit, and more tourist information, refer to the Provincetown road trip website.

You can fly from Boston to Provincetown in 2 hours. Alternatively, you can ride a ferry; or drive. October in Provincetown sees daily highs of 63°F and lows of 49°F at night. Wrap up your sightseeing on the 5th (Thu) early enough to drive to Sandwich.

Things to do in Provincetown

Parks · Outdoors · Beaches · Museums

Side Trips

Sandwich

— 6 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Get out of town with these interesting Sandwich side-trips: New Bedford (Hurricane Barrier Harbor Walk & New Bedford Whaling Museum), Stone Bridge Farm (in Acushnet) and Mayflower Cranberries (in Plympton). There's still lots to do: engage your brain at Sandwich Glass Museum, visit a coastal fixture at Nobska Point Lighthouse, get engrossed in the history at The Jenney, and make a trip to Old King's Hwy.

To see maps, ratings, photos, and more tourist information, read Sandwich online attractions planner.

Getting from Provincetown to Sandwich by car takes about 1.5 hours. Other options: take a bus. November in Sandwich sees daily highs of 53°F and lows of 35°F at night. Wrap up your sightseeing on the 11th (Wed) to allow time to travel to Oak Bluffs.

Things to do in Sandwich

Museums · Historic Sites · Parks · Outdoors

Side Trips

Oak Bluffs, Martha's Vineyard

— 5 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Explore the numerous day-trip ideas around Oak Bluffs: Aquinnah (Gay Head Lighthouse & Aquinnah Lighthouse). Next up on the itinerary: steep yourself in history at Trinity Park Tabernacle, walk around Ocean Park, visit Martha's Vineyard Camp meeting Association (MVCMA), and stroll through Sheriff's Meadow Sanctuary.

Find out how to plan Oak Bluffs trip without stress by asking Inspirock to help create an itinerary.

You can do a combination of taxi and ferry from Sandwich to Oak Bluffs in 1.5 hours. Alternatively, you can do a combination of bus and ferry. In November in Oak Bluffs, expect temperatures between 53°F during the day and 37°F at night. Wrap up your sightseeing on the 16th (Mon) early enough to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Historic Sites · Parks · Wildlife · Outdoors

Side Trips

Nantucket

— 7 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, and historic sites. Your trip includes some of its best attractions: enjoy the sea views from Great Point Light, tee off at Miacomet Golf Club, get to know the fascinating history of Milestone Bog, and don't miss a visit to Old Mill.

For photos, where to stay, ratings, and other tourist information, refer to the Nantucket itinerary maker site.

Getting from Oak Bluffs to Nantucket by ferry takes about 2 hours. Expect a daytime high around 53°F in November, and nighttime lows around 41°F. Finish up your sightseeing early on the 23rd (Mon) so you can travel to Lenox.

Things to do in Nantucket

Historic Sites · Parks · Outdoors · Beaches

Lenox

— 6 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Change things up with these side-trips from Lenox: Adams (Mount Greylock & Ashuwillticook Rail Trail), Westfield (Amelia Park Children's Museum & Stanley park) and Chester Railway Station (in Chester). There's still lots to do: explore the world behind art at Norman Rockwell Museum, take your sightseeing to a higher altitude at Monument Mountain, take in the spiritual surroundings of National Shrine of the Divine Mercy, and experience rural life at Bartlett's Orchard.

To see traveler tips, ratings, maps, and more tourist information, read Lenox trip builder website.

You can do a combination of ferry and car from Nantucket to Lenox in 6.5 hours. Other options are to do a combination of flight and bus; or do a combination of ferry and bus. Plan for slightly colder temperatures traveling from Nantucket in November, with highs in Lenox at 47°F and lows at 28°F. Wrap up your sightseeing on the 29th (Sun) early enough to drive back home.

Things to do in Lenox

Museums · Parks · Historic Sites · Nature

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.