Boston, Massachusetts to Portland, Maine: An Extraordinary Fall 'Bloom' Route

147 miles - At least 4 hours

The New England coast offers pleasant, gorgeous drives any time of year, but especially when fall foliage is at its peak of coloration. In a day's journey, one can compete in a race, observe witches, go whale-watching, jump in a kayak, stroll through a castle and climb to the top of a lighthouse or two. There will probably be at least one or two other road trippers sharing the road with you, so slow down and enjoy the New England crawl.



Here are a few highlights of this route.

Boston, Massachusetts (Starting point)
A majestic old city in which you could easily spend many days exploring and tracing the historical roots of the nation. But if you only have 3 or 4 hours, and you also have 3 or 4 companions, I especially recommend Urban Interactive, a competitive, informative and fun scavenger hunt that is staged at Boston Common during the warmer months. With the aid of i-phones issued by the attendants, you and your teammates will race against another team to find clues and solve a puzzle, while learning about the city's past, including some tidbits that are often overlooked in the history books. A hilarious, unforgettable introduction to Beantown!

Salem, Massachusetts (Mile 21)
Driving along the coast on MA 1A, you'll come to the enchanting City of Witches, which contains more history (some of it rather dark) per square foot than just about any city you'll ever visit. Salem takes pride in the number of practicing witches now so keep your wits about you....There are many museums and historical sites but the following are especially worthwhile: Burying Point, the oldest cemetery in Salem (dating from 1637), next to it is the Salem Witch Trials Memorial, dedicated on the 300th anniversary of that tragic event. 'Cry Innocent' is a theatrical production at Old Town Hall reenacting the trial of young Bridget Bishop, with the audience serving as the jury. Salem is an especially good town for taking a candlelight 'ghost tour,' and it's the perfect place to be for Halloween, when the whole downtown is closed to traffic and becomes just one big costume party.

Gloucester, Massachusetts (Mile 41)
Continuing up the coast on MA 127, you come to this sleepy little city, the ideal place to go if you're interested in a whale watching expedition. There's also a nice little beach that often isn't crowded. And there's Hammond Castle, a medieval-style home built nearly a century ago by inventor John Hays Hammond, Jr., who held more patents (over 400) than any American but Edison. He also collected ancient artifacts, and you can view many of them on a self-guided tour. And as you might expect, the castle is another excellent place to drop in at Halloween.

Newburyport, Massachusetts (Mile 65)
From Gloucester, take MA 133, which takes you back to 1A, and on to Newburyport. A quaint and quiet resort town, where residents delight in growing seasonal flowers. This is also the only place in the country (if not the whole world) where you can have dinner at the top of a lighthouse.

Portsmouth, New Hampshire (Mile 87)
Portsmouth, is a superb location to go kayaking on coastal waterways. If you have even more time to spend, strongly consider a tour of the Isles of Shoals.

Kennebunkport, Maine (Mile 116)
Long noted as the place where the wealthy get away from it all - the Bush family has maintained a summer home here for several generations. Kennebunkport is a quiet but powerful serving of Yankee charm, I would characterize it as a bed-and-breakfast shangri-la. Shop for gifts for the person who has everything, or take a seaside stroll, or just unwind.

Portland, Maine (Mile 147)
Your journey ends here, in a culturally and historically rich major city, with lots of night life. But also be sure to visit the Portland Observatory, at 138 Congress St., which bills itself as 'the only known remaining historic maritime signal tower in the United States.' You'll get an awe-inspiring view of that coast you've been driving on for the last few hours.