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.

Emma Watson has become the latest target of the 4Chan nude hacking scandal
peopleThreats follows actress' speech on feminism and equality at the UN
Life and Style
food + drink
Arts and Entertainment
British actor Idris Elba is also a DJ and rapper who played Ibiza last summer
Life and Style
Have you tried new the Independent Digital Edition apps?
ebookHow to enjoy the perfect short break in 20 great cities
Life and Style
Life and Style
Alan Turing, who was convicted of gross indecency in 1952, was granted a royal pardon last year
Arts and Entertainment
Sheridan Smith as Cilla Black and Ed Stoppard as her manager Brian Epstein
tvCilla Episode 2 review: Grit under the glamour in part two of biopic series starring Sheridan Smith
Life and Style
Independent Travel Videos
Independent Travel Videos
Simon Calder in Amsterdam
Independent Travel Videos
Simon Calder in Giverny
Independent Travel Videos
Simon Calder in St John's
Independent Travel Videos
Latest stories from i100
Have you tried new the Independent Digital Edition apps?
Independent Dating

By clicking 'Search' you
are agreeing to our
Terms of Use.

ES Rentals

    iJobs Job Widget
    iJobs Travel

    Food and Beverage Cost Controller

    18,000 to 20,000 per annum: Accountancy Action: Our fantastic leisure client i...

    Affiliate Marketing Manager / Affiliate Manager

    £50 - 60k (DOE): Guru Careers: An Affiliate Marketing Manager / Affiliate Mana...

    IT Administrator - Graduate

    £18000 Per Annum: Clearwater People Solutions Ltd: ***EXCELLENT OPPORTUNITY FO...

    USA/Florida Travel Consultants £30-50k OTE Essex

    Basic of £18,000 + commission, realistic OTE of £30-£50k : Ocean Holidays: Le...

    Day In a Page

    Secret politics of the weekly shop

    The politics of the weekly shop

    New app reveals political leanings of food companies
    Beam me up, Scottie!

    Beam me up, Scottie!

    Celebrity Trekkies from Alex Salmond to Barack Obama
    Beware Wet Paint: The ICA's latest ambitious exhibition

    Beware Wet Paint

    The ICA's latest ambitious exhibition
    Pink Floyd have produced some of rock's greatest ever album covers

    Pink Floyd have produced some of rock's greatest ever album covers

    Can 'The Endless River' carry on the tradition?
    Sanctuary for the suicidal

    Sanctuary for the suicidal

    One mother's story of how London charity Maytree helped her son with his depression
    A roller-coaster tale from the 'voice of a generation'

    Not That Kind of Girl:

    A roller-coaster tale from 'voice of a generation' Lena Dunham
    London is not bedlam or a cradle of vice. In fact it, as much as anywhere, deserves independence

    London is not bedlam or a cradle of vice

    In fact it, as much as anywhere, deserves independence
    Vivienne Westwood 'didn’t want' relationship with Malcolm McLaren

    Vivienne Westwood 'didn’t want' relationship with McLaren

    Designer 'felt pressured' into going out with Sex Pistols manager
    Jourdan Dunn: Model mother

    Model mother

    Jordan Dunn became one of the best-paid models in the world
    Apple still coolest brand – despite U2 PR disaster

    Apple still the coolest brand

    Despite PR disaster of free U2 album
    Scottish referendum: The Yes vote was the love that dared speak its name, but it was not to be

    Despite the result, this is the end of the status quo

    Boyd Tonkin on the fall-out from the Scottish referendum
    Manolo Blahnik: The high priest of heels talks flats, Englishness, and why he loves Mary Beard

    Manolo Blahnik: Flats, Englishness, and Mary Beard

    The shoe designer who has been dubbed 'the patron saint of the stiletto'
    The Beatles biographer reveals exclusive original manuscripts of some of the best pop songs ever written

    Scrambled eggs and LSD

    Behind The Beatles' lyrics - thanks to Hunter Davis's original manuscript copies
    'Normcore' fashion: Blending in is the new standing out in latest catwalk non-trend

    'Normcore': Blending in is the new standing out

    Just when fashion was in grave danger of running out of trends, it only went and invented the non-trend. Rebecca Gonsalves investigates
    Dance’s new leading ladies fight back: How female vocalists are now writing their own hits

    New leading ladies of dance fight back

    How female vocalists are now writing their own hits