All The History, Culture and Scenery You Could Ask For

28th September 2018

Some destinations just lend themselves to certain times of the year. New England – in the fall – is one of them. But, as Jennifer Lipman discovers, this is a holiday location that’s more than just a one-season wonder.

What you notice, as you travel around its cities and towns, is that everywhere in New England looks just like a film set. The Atlantic coastal region – stretching from Maine near the Canadian border to more southerly Rhode Island and Connecticut as you approach New York – belongs in an episode of Dawson’s Creek or on a Christmas card; all pastel-coloured clapboard houses with white picket fences, acres of foliage and jaunty road signs announcing that you’re entering Main Street or Broad Street.

Open that Christmas card, and there’s plenty to see and do in a part of the world that’s chock-full of history, personality and stunning scenery, and yet isn’t always fully explored by Britons, who tend to head to Boston but rarely venture much further.

Naturally, for the full New England experience one should go there in ‘the fall’, when the leaves on the many, many trees are turning those signature fire reds and oranges, and there are pumpkins grinning at you from every stoop or restaurant window. And if you’re planning on taking in the bucolic beauty of the Berkshires, in Western Massachusetts, or heading to the famous White Mountains, that season is certainly your best bet; be sure to make a stop off in Stockbridge, hometown of the famous illustrator Norman Rockwell, where a dedicated gallery shows off his vast oeuvre, and in nearby Lenox, where you can tour the home of the acclaimed novelist Edith Wharton.

If you’re on the hunt for fishing villages and sea views, however, the New England season for the locals stretches from May into the autumn, giving you more choice of when to visit – although for those auburn leaves September and October would still be most advisable. But even earlier in the spring or later in the year there’s no reason to stay away (except perhaps in deepest winter; snow is no joke in these parts). Whenever you go, make sure you hire a car as transport links leave much to be desired.

We started in Portland, the busiest spot in Maine, although that’s not saying much. It’s a place that has enjoyed something of a renaissance in recent years. A harbour town, the smell of saltwater hangs in the air and you can scarcely move for shacks flogging lobster rolls, clams or crab cakes, with numerous boat trips and whale-watching cruises on offer. It’s a sleepy holiday destination, set apart by the array of impressive art galleries and bijou design shops scattered around Congress and Exchange Streets (warning: the folksy charm of the place doesn’t mean necessarily that it’s affordable). Stop in for an afternoon, wash down your seafood lunch with a delicious handmade potato-based treat from The Holy Donut, and enjoy the slower pace of life for a change.

From Portland it’s a short drive to the 90-acre Fort Williams Park, Cape Elizabeth, where there is a manageable coastal walk with breathtaking views and the impressive Portland Head Light to admire. Then head south to Kennebunkport for a night or two. Best known as the summer home of the Bush family, and still a destination that well-heeled families return to year after year, it’s a winsome beach town with a good game in smart restaurants, picture-perfect inns, and stores selling high end tourist tat or local delicacies including Maine blueberry jam, saltwater taffy or speciality infused olive oil. Enjoy a cocktail and a hearty meal at Federal Jack’s Brew Pub for the best sunset dining experience.

The town itself is tiny, but on the roads nearby you’re spoiled for choice for places to stay. We spent two nights basking in the friendly hospitality and peace of the chintzy Maine Stay Inn, with its gourmet breakfasts on a sunny balcony, detail-focused owners, and location just a few minutes’ walk away from the main street and not much further from a lovely stretch of sand.
We needed the breather, because then it was on to Boston, about two hours’ drive away. It isn’t quite as frenetic as New York but it’s nonetheless trying hard to keep up. Like all big cities – especially centres of history – there are museums and galleries aplenty, not least the JFK Presidential Library where Cold War buffs or those nostalgic for soaring oratory will find plenty to amuse. But put on your walking shoes because the best way to experience The Hub (as Boston is nicknamed) is on foot. The 2.5 mile Freedom Trail, which takes you from the glorious Boston Common and the Massachusetts State House through the Italian neighbourhoods of North End (stop for a Cannoli oozing with any filling you could hanker for at local landmark Mike’s Pastry) and across the Charles River is an exhausting but rewarding whirlwind tour through the city’s past. As a Brit, it’s an edifying and occasionally mortifying lesson in our history too, since many of the sites highlight the British troops’ poor behaviour in the run up to American independence.

You could easily spend a week in Boston, but we only had two nights and still managed to cram everything in. Make time to watch the sun go down over the harbour, take a tour of Harvard University over the river in Cambridge (and smirk as your guide waxes lyrical about how ancient these 200-year-old buildings are) and wander the pretty cobbled streets of Beacon Hill.

Then it was onwards to the Cape, the summer destination of the Kennedys and all classy Bostonians. When locals talk about it they often do so as if it were one place, when the reality is it covers a vast stretch of land as well as two key islands: Martha’s Vineyard and Nantucket. All have merits but we opted for the smaller, Nantucket, about an hour’s ferry from Hyannis Port.
“It’s quieter than the Vineyard,” a regular visitor told me on the crossing, but it’s far from dull, not to mention absurdly quaint.

You dock and immediately arrive in the centre of town, home to impossibly fancy restaurants and shops, as well as the infamous Whaling Museum, which delves into the island’s pre-tourism history. The majority of Nantucket is residential (largely vacation homes) and it’s essentially a game of ‘spot the fancy mansion’, as each estate appears impossibly grander than the next. If you’ve got time, hire bikes or a car to set off for the other side of the island, where the coastline is even more impressive.

Stay at the centrally-located 21 Broad, which offers lavish rooms and a peaceful courtyard, and dishes up artisan baked goods in the morning. It’s got all the accoutrements you’ll want for the beach too; towels were handily left for us in canvas bags, with chairs and umbrellas on hand to borrow.

There’s hardly a restaurant on Nantucket that doesn’t offer trendy food and drink, but save room for an ice cream at The Juice Bar (warning: cash only), where the waffle cones are baked in front of your eyes and the flavours list goes on forever. Adult-only parties should try to stretch to drinks (or even dinner) at the uber-posh beachside bistro Galleys.

While Bostonians tend to ‘summer’ in Nantucket, we moved swiftly on, hopping along to Newport, Rhode Island, once the premier such spot of the East Coast. Newport’s claim to fame dates back to the so-called Gilded Age at the turn of the last century, when billionaires made it their polo playground – and you can see why. Along the coast (with the best views coming from a public walkway, the 3.5mile Cliff Walk) every house is a bona-fide mansion, from Rosecliff to the erstwhile Vanderbilt home, Breakers. Both are open to tour; the latter is a Trumpian monstrosity of lavishly expensive furnishings and a total absence of taste – in other words, it’s a must see.

Modern Newport is a mix of super-yachts and a low-key beach town with a chilled, younger vibe than further up the coast; worth a night at least. Set up to be tolerant of all religions, the city is also home to the country’s oldest synagogue, the Touro, which offers guided tours, as well as an impressive collection of 19th century artwork at the National Museum of American Illustration.

So whether you’re visiting in spring, summer or fall, there you have it; New England in a week, and all the history, culture and scenery you could ask for.

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