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Top 30 Destinations by Personality Type
Venturers Journeyers
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Did You Know…?

  • Harvard houses the world’s largest university library — more than 13 million books.
  • Massachusetts was the first state to adopt a constitution (1780), and it is the world’s oldest still in use.
  • The American colonies’ first post office was opened at a tavern in Boston in 1639.
  • Basketball was invented in Springfield (1891) to give athletes an indoor winter sport.
  • The Boston News-Letter was America’s first regularly issued newspaper (1704).

From history to seaside holidays

The first Thanksgiving occurred in Massachusetts, the American Revolution started in Massachusetts and the state is linked to a wide range of historical figures — John Adams, Paul Revere, Henry Wadsworth Longfellow, among others — and places associated with the making of America. There is much to engage the history buff.

Besides, Massachusetts is an attractive coastal state with charming New England towns, fall foliage colors, a shoreline and islands that visitors seek for holidays.  And, it has its capital Boston, one of America’s better-favored cities, noted for its historic center, great restaurants (especially, the seafood), shopping options and a vibrant cultural life.

All personality types like the same things about the state. The places they mention most are primarily limited to Boston, Cape Cod and the islands of Martha’s Vineyard and Nantucket. The picturesque north shore, the middle portion of the state, the western half and the quaint, historic towns located a short distance inland are largely ignored.

The state has the advantage of being both rural and urban, of having in close proximity big-city amenities and seaside charms. The state is seen as relaxing, a characteristic that appeals to people who choose this extraordinarily historic part of the original colonies.

Those who like Massachusetts talk about how calm they feel when they visit; there’s plenty to do, but no sense of urgency to do it. Cape Cod and Nantucket especially contribute to this feeling. Visitors talk about the islands’ sense of isolation, their unspoiled qualities, a very natural kind of beauty and the friendly local people.

When travelers talk about Boston, their respect and reverence for its contribution to the beginnings of the nation are apparent. The charm of the city (plus its convenient public transportation system) and the rich and varied kinds of food available in its restaurants also receive many favorable comments.

For those who need to unwind, Massachusetts may be just the place for relaxing settings — and for gently paced explorations of the countryside.  Surprisingly, no one in our surveys spontaneously mentioned the fall colors. They can be as spectacular in Massachusetts as elsewhere in New England.

Things to do for Venturers

  • Sign up to compete in the Pittsfield Winter Carnival Cross-Country Ski Race at the Canterbury Farm Cross-Country Ski Center. The February event is said to attract “some of the best and worst skiers in the Berkshires.”
  • Run in the Boston Marathon if you can qualify.
  • Go sailing at Marblehead — or at a whole raft other places in Massachusetts.
  • Stay in a haunted bed-and-breakfast establishment. A couple of examples: Nichols Guest Rooms, Seekonk, for one or more spirits playing with the lights and fostering other mischief in the night, or Thaddeus Clapp House, Pittsfield, for a ghost who is described as friendly and a member of the founding Clapp family.
  • Kayak along the Ipswich River, or make that the Deerfield River.
  • Take lessons in mushing sled dogs, or bring your own dog for his own lessons in pulling a sled (if the dog is cut out for this).  Or, just take a dogsledding excursion of an hour, a few hours or a full day.

Things to do for Centrics

  • Overnight at the Lizzie Borden Bed and Breakfast in Fall River. This Victorian house was the scene of the axe murders in 1892 of Andrew and Abby Borden, possibly by his daughter Lizzie; you can rent the bedroom where Abby was killed.  After a breakfast “reminiscent” of the Bordens’ last breakfast, go to the Fall River Historical Society’s museum to see the really gory stuff.
  • Attend the highly regarded Tanglewood Music Festival, held in the Tanglewood Music Shed near Lenox in the Berkshires and the summer home of the Boston Symphony Orchestra.
  • Ride the Cranberry Country Train in South Carver where the Edaville Railroad takes passengers in vintage passenger cars for a 5.5-mile trip through working cranberry bogs. You also can visit bogs in pony-drawn wagons or even view them from a helicopter.
  • Climb the spiral staircase to the top of Boston’s Bunker Hill Monument, a 221-foot obelisk. The monument memorializes a Revolutionary War battle.
  • Travel the Mohawk Trail in northwest Massachusetts. Now Route 2, it originated as a Native American trail. Choose it as your fall foliage route.
  • See 50-foot, 40-ton whales a mere 25 miles off the Massachusetts coast, any time from April to October. The World Wildlife Fund named the state one of the world’s 10 best places to watch the world’s largest mammal.

Things to do for Authentics

  • Stroll the Black Heritage Trail celebrating Boston’s 19th century black community.
  • Educate or entertain yourself at the American Sanitary Plumbing Museum in Worcester, Mass. Or, consider the Museum of Bad Art, Dedham, Mass., an assemblage of art “too bad to be ignored” hung in a theater basement but “conveniently located just outside the men’s room.”
  • Visit a house made entirely of paper, the Paper House in Rockport. Its builders, in the 1920s, used more than 100,000 rolled and pasted newspapers to make and furnish the two-room house. A writing desk is made from accounts of Charles Lindbergh’s 1927 solo transatlantic flight.
  • Book a re-created 1627 harvest dinner, offered on select October and November dates, or attend the all-day Thanksgiving celebration at Plimoth Plantation. Or, also in autumn, attend a cranberry harvest event, such as the October Annual Harvest Celebration in Wareham which offers free cranberry harvest tours to the bogs.
  • Stay at the 10-room Longfellow’s Wayside Inn in Sudbury, Mass., which was immortalized by Henry Wadsworth Longfellow in his 1863 book of poems called “Tales of a Wayside Inn.” The innkeeper at the time, Lyman Howe, was the featured character in the book’s Landlord’s Tale, in which Longfellow gave us the phrase, “Listen my children and you shall hear, of the midnight ride of Paul Revere.”
  • Just to say you did it, drive to Chargoggagoggmanchauggagoggchaubunagungamaugg, a lake in Webster; it has the longest place name in the U.S.

Additional Resources

For more information, consult the Massachusetts Office of Travel and Tourism at