Trail Of The Unexpected: Martha's Vineyard is a New England getaway fit for a president

It has already been a busy summer in Martha's Vineyard. In this, as in every year, a seasonal onslaught of "off-islanders" multiplies its 15,000-strong population several times over. But now, the tourists have been joined by Secret Service personnel, here to prepare for the First Family's arrival tomorrow.

Martha's Vineyard is a small island five miles off the coast of Massachusetts. It is also the perfect choice for the Brand Obama blend of understated glamour. For while the presidential visit will undoubtedly cause a ripple of excitement, islanders (known as "Vineyarders") will be taking it all in their stride, undoubtedly most concerned about the effects on the local traffic.

This tranquil triangle of seaside New England – roughly twice the size of the Channel Island of Jersey – is accustomed to more than its fair share of high-profile visitors. The former president Bill Clinton holidayed here while in office; media moguls and film directors such as Spike Lee and Wes Craven mingle with East Coast blue bloods and members of political dynasties; Caroline Kennedy owns an oceanside compound on Chappaquiddick.

Those looking for the quiet life melt across the island to summerhouses and magnificent compounds with sea views tucked down anonymous, bosky lanes. According to the Vineyard Gazette, the Obamas are due to stay at the $20m Blue Heron Farm in sought-after Chilmark, rented from the fabulously wealthy Van Devender family for a figure rumoured to be about $30,000 per week.

Although an extreme example, properties such as these encapsulate the discreet New England aesthetic: a cluster of shingle buildings buried in verdant gardens, all with the requisite panoramic views of the water.

It might be a high price to pay, but what Mr Obama, his wife, Michelle, and daughters Malia and Sasha will be getting is the chance to occupy a blissful corner of America to play out a rural seaside fantasy. Most visitors are drawn here by the chance to kick back and enjoy life's simple pleasures – strolls down deserted beaches, bicycle rides and regular fishing trips.

On my first afternoon there, I found myself crouching in the middle of a pick-your-own farm searching out the juiciest strawberries – the perfect way to pass a few hours – and the next day kicked off with an early-morning fishing trip in search of striped bass. On the other hand, I also got to mingle with Park Avenue princesses at a cocktail party. As I surveyed the stunning views out to sea, I also began to take note of some of the guests' name badges. The surnames read like the entries of an American Who's Who.

Despite this, most Vineyarders take pride in the fact their 4x4s are more beaten up than those on their even more affluent neighbour Nantucket, with which there is a good-humoured but slightly barbed rivalry.

Oak Bluffs was home to the Vineyard's first summer resort, and is still one of the first stops on most sightseeing itineraries. In 1835, part of its centre became a Methodist camp meeting place, which has now become one of town's most photographed architectural curiosities. Over time, the tents evolved to the present spectacle of the 300 or so gingerbread-style wooden cottages painted a rainbow of colours, packed along the narrow streets.

The prim, manicured Edgartown on the island's north-east coast is the best place to get a feeling of Martha's Vineyard's prosperous past. Originally known as Great Harbor, it was the site of the island's first white settlement, established in 1642 by Thomas Mayhew Junior, who bought it, along with the neighbouring Elizabeth Islands, from two English aristocrats for £40. Here, I strolled streets lined with houses built for the ships' captains, their gardens groaning under a weight of hydrangea blooms. There are countless boutiques selling the preppy garb beloved of female visitors to the island, for whom Michelle Obama is an obvious style icon.

But again and again, it's the pastoral charm of the island that strikes you. Drive what is still referred to as "up-island" (or west) through West Tisbury and Chilmark and you are soon enveloped in scenes of handsome, shingle farmhouses framed by swaying meadows, dry-stone walls, clumps of woodland and quaint roadside farm stands selling locally grown fruit and vegetables. Very little disturbs the peace – not even the traffic, which has a 20mph speed limit.

Day-trippers arriving at Oak Bluffs and Vineyard Haven from the Cape Cod mainland tend to board one of the distinctive pink trolley bus tours for a whistle-stop tour of the island's six towns.

But for residents, however temporary, there is a chance for proper immersion. A couple of miles west of the private stretch of Squibnocket beach that the Obamas will no doubt be enjoying next week is one of the island's main scenic attractions: the towering, wind-buffeted cliffs of Gay Head. Beyond, past Aquinnah lighthouse towards Vineyard Haven, the Obamas may well come across the impossibly picturesque Menemsha, a string of greying fishing shacks clustering round a dock that found fame as a location for Jaws.

Perhaps the First Family will even be counted among those who have stopped at The Bite, a tiny shack a short walk up the road. As I stood in line waiting to order through the tiny hatch, a local confided that the quahog clam chowder was the best on the island.

As I sat at a cobalt-blue picnic table, sipping the chowder from a cardboard cup (with some crisp, deep-fried calamari as an accompaniment), I could not help but agree. It was worthy of any president who might be passing by.

Getting there

Ferries are operated by the Steamship Authority (001 508 477 8600; steamshipauthority. com). Cape Air (001 508 771 6944; has regular services from Boston.

Staying there

Lambert's Cove Inn, 90 Manaquayak Road, Vineyard Haven (001 508 693 2298; B&B from $175 (£117).

Eating and drinking there

The Bite, 29 Basin Road, Menemsha (001 508 645 9239;

More information; 001 617 973 8500 or; 001 508 696 7400.

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