Delineated by a 2.5-mile-long red-brick (or paint) stripe in the sidewalk, the Freedom Trail stretches from Boston Common to Charlestown, linking sixteen points “significant in their contribution to this country’s struggle for freedom”. About half the sights on the trail are related to the Revolution itself; the others are more germane to other times and topics.

Though some of the touches intended to accentuate the trail’s appeal move closer to tarnishing it (the costumed actors outside some of the sights, the pseudo-antique signage), the Freedom Trail remains the easiest way to orient yourself downtown, and is especially useful if you’ll only be in Boston for a short time, as it does take in many “must-see” sights.

 Detailed National Park Service maps of the trail can be picked up from the visitor centre. Thrifty travellers take note: most stops on the trail are either free or inexpensive to enter.

Later I discovered the Hamptons, with its designer shops and sleek nightclubs. The Cape began to feel a bit "ye olde" by comparison; the fudge shops and five-and-dimes didn't have quite the same allure. But something funny happened in my absence: the Cape stayed the same. When I started coming back after years away, I fell in love with its unpretentious charms all over again. Granted, there's now a Marc Jacobs store in Provincetown, but my childhood shell shop remains tucked away behind the saltwater taffy store. And despite the influx of big money in Chatham, the town band still plays in the park on summer Friday nights and local fire trucks still lumber down Main Street in the annual Fourth of July parade.

Life hasn't changed much thanks in part to the locals: Cape Codders are a fiercely protective bunch—a reputation confirmed for me firsthand while I was eating day-boat scallops recently at Abba, a restaurant in Orleans. I made the mistake of telling some fellow diners that I was writing a story on the area. Suddenly they were all over me for my credentials. Did I have a place here?(Luckily, my parents bought a house in East Harwich a few years ago.) What was my favorite beach?Lobster roll?Hiking trail?It was quite an interrogation, but I passed. I guess I had earned my stripes—and the right to lead others to my favorite spots.

Martha's Vineyard, Massachusetts

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Martha's Vineyard

A modern American city that proudly trades on its colonial past, Boston is about as close to the Old World as the New World gets. This is not to say it lacks contemporary attractions: its cafés, museums, neatly landscaped public spaces and diverse neighbourhoods are all as alluring as its historic sites.

 Boston has grown up around Boston Common, a utilitarian chunk of green established for public use and “the feeding of cattell” in 1634. A good starting point for a tour of the city, it is also one of the links in the string of nine parks called the Emerald Necklace. Another piece is the lovely Public Garden, across Charles Street from the Common, where Boston’s iconic swan boats paddle the main pond. Grand boulevards such as Commonwealth Avenue lead west from the Public Garden into Back Bay, where Harvard Bridge crosses into Cambridge. The beloved North End, adjacent to the waterfront, is Boston’s Little Italy, its narrow streets chock-a-block with excellent bakeries and restaurants. Behind the Common rises the State House and lofty Beacon Hill, every bit as dignified as when writer Henry James called Mount Vernon Street “the most prestigious address in America”.

The states of Massachusetts, Rhode Island, Connecticut, Vermont, New Hampshire and Maine – collectively known as New England – exemplify America at its most nostalgic: country stores that brim with cider and gourds, snow-dusted hillsides, miles of blazing autumn foliage, clam shacks, cranberry bogs and an unruly ocean that distinguishes and defines it all.


Scratch just beneath the surface, and you’ll also uncover fiercely independent locals, innovative chefs, some of the country’s best contemporary art museums and a profound sense of history.

Boston especially is celebrated as the birthplace of American independence – so many seminal events took place here, or nearby at Lexington and Concord. New England was also home to many of the preeminent figures of American literature, from Mark Twain and Henry Thoreau to Emily Dickinson and Jack Kerouac. The Ivy League colleges – Harvard, Yale, Brown, Dartmouth et al – are the oldest in the country and remain hugely influential, continually channelling new life into towns like Cambridge and New Haven and setting a decidedly liberal tone throughout the region.

To the east, the peninsula of Cape Cod flexes off Massachusetts like a well-tanned arm. Here you will find three hundred miles of shoreline, sea roses, tumbling sand dunes and the fantastic isles of Nantucket and Martha’s Vineyard. In the western part of the state, the tranquil Berkshires offer the best in summer festivals as well as fascinating art museums. The sights of Connecticut and Rhode Island tend to be urban, but away from I-95 you’ll find plenty of tranquil pockets, particularly in the way of Newport and Block Island, fifty miles south of Providence. Boston is a vibrant and enchanting city from which to set off north, where the population begins to thin out (and the seafood gets better as you go). The rest of Massachusetts is rich in historical and literary sights, while further inland, the lakes and mountains of New Hampshire and Maineoffer rural wildernesses to rival any in the nation. Maine is especially known for its coastline, dotted with lighthouses and wild blueberry bushes. The beloved country roads of Vermont offer pleasant wandering through rural towns and serene forests; during your travels, be sure to pick up some maple syrup, a local delicacy, for your pancakes back home.

The best time to visit New England is in late September and October, when visitors flock to see the magnificent autumn foliage. Particularly vivid in Vermont, it’s an event that’s not to be missed.*

Featured Region: New England

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Beacon Hill, Boston

The Freedom Trail, Boston

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Massachusetts

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The state of Massachusetts was established with a lofty aim: to become, in the words of seventeenth-century governor John Winthrop, a utopian “City upon a hill”. This Puritan clarity of thought and forcefulness of purpose can be traced from the foundation of Harvard College in 1636, through the intellectual impetus behind the Revolutionary War and the crusade against slavery, to the nineteenth-century achievements of writers such as Melville, Emerson, Hawthorne and Thoreau.

Spending a few days in Boston is strongly recommended.

 Perhaps America’s most historic city, and certainly one of its most elegant, it offers a great deal of modern life as well, thanks in part to the presence of Cambridge, the home of Harvard University and MIT (Massachusetts Institute of Technology), just across the river. Several historic towns are within easy reach – Salem to the north, known for its “witch” sights,Concord and Lexington, just inland, richly imbued with Revolutionary War history, and Plymouth, to the south, the site of the Pilgrims’ first settlement (1620).

One of the most celebrated slices of real estate in America, Cape Cod boasts a dazzling, three-hundred-mile coastline with some of the best beaches in New England. A slender, crooked peninsula, it’s easily accessed from the region’s snug villages, many of which have been preserved as they were a hundred or more years ago. Today, much of the land on the Cape, from its salt marshes to its ever-eroding dunes, is considered a fragile and endangered ecosystem, and once you head north to the Outer Cape, past the spectacular dunes of Cape Cod National Seashore, you get a feeling for why this narrow spit of land still has a reputation as a seaside wilderness. Provincetown, at the very tip of Cape Cod, is a popular gay resort and summer destination for bohemians, artists and fun-seekers lured by the excellent beaches, art galleries and welcoming atmosphere.

Just off the south coast of Cape Cod, the relatively unspoiled islands of Martha’s Vineyard and Nantucket have long been some of the most popular and prestigious vacation destinations in the USA. Both mingle an easy-going cosmopolitan atmosphere and some of the best restaurants and B&Bs on the East Coast. Nantucket is usually considered the more highfalutin’ of the pair, teased for its preppy fashions; Martha is more expansive and laidback, known for its elaborate gingerbread-style houses, wild moorlands and perfect beaches.

Western Massachusetts is best known for the beautiful Berkshires, which host the celebrated Tanglewood summer music festival and boast museum-filled towns such as North Adams and Williamstown – both in the far northwest corner of the state, at the end of the incredibly scenic Mohawk Trail. Amherst and Northampton are stimulating college towns in the verdant Pioneer Valley, with all the cafés, restaurants and bookstores you could want.


No visit to Boston would be complete without an afternoon spent strolling around delightful Beacon Hill, a dignified stack of red brick rising over the north side of Boston Common. This is the Boston of wealth and privilege, one-atime home to numerous historical and literary figures – including John Hancock, John Quincy Adams, Louisa May Alcott and Oliver Wendell Holmes.

 

As you walk, keep an eye out for the purple panes in some of the townhouses’ windows (such as nos. 63 and 64 Beacon St). At first an irritating accident, they were eventually regarded as the definitive Beacon Hill status symbol due to their prevalence in the windows of Boston’s most prestigious homes.

Cape Cod, Massachusetts

The largest offshore island in New England, twenty-mile-long MARTHA’S VINEYARD encompasses more physical variety than Nantucket, with hills and pastures providing scenic counterpoints to the beaches and wild, windswept moors on the separate island of Chappaquiddick.

Martha’s Vineyard’s most genteel town is Edgartown, all prim and proper with its freshly painted, white clapboard colonial homes, museums and manicured gardens.

The other main settlement, Vineyard Haven, is more commercial and one of the island’s ferry ports. Oak Bluffs, in between the two (and the other docking point for ferries), has an array of fanciful wooden gingerbread cottages and inviting restaurants. Be aware of island terminology: heading “Up-Island” takes you southwest to the cliffs at Aquinnah (formerly known as Gay Head); conversely, “Down-Island” refers to the triumvirate of easterly towns mentioned here.

Boston: Drinking & Nightlife

My father used to say that you were guaranteed good weather if you spotted a boat as you drove across the Cape Cod Canal—the thin strip of water that separates the 70-mile-long peninsula from mainland Massachusetts. As our Ford Pinto station wagon rattled over the Sagamore Bridge, my brother and I would press our foreheads to the window and hope for a sighting. To this day, I religiously scan the water every time I hit the bridge. It's my signal to myself that I have left the real world behind—and it's just as reassuring as that first whiff of briny air or the sight of pine needles mixed with sand along the roadside.

When I was growing up, my family rented shingled cottages in Chatham or Dennis, or stayed with friends in a beachfront apartment in Provincetown or a Victorian house in Harwich. A vacation on Cape Cod was all about simple pleasures: fishing off the Chatham drawbridge with my grandfather, putt-putt golfing in Dennisport, watching movies at the Wellfleet Drive-In Theatre (I saw Jaws there and, like half the country, was terrified to go in the water for years afterward). On sunny mornings, we'd debate whether to make the trek to the wide, wild beaches of the National Seashore or head to one of the placid coves on nearby Nantucket Sound. Gray days meant decamping to Provincetown, where my brother and I would create spin-art masterpieces at a toy shop while our parents explored the galleries. No trip to the Cape was complete without a platter of fried clams from a roadside shack.

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Boston, Massachusetts