Inn Season : Destination: California & Massachusetts : Five quirky towns, five charming hotels--its a match made in Martha’s Vineyard


The island of Martha’s Vineyard, a 23-by-9-mile patch of real estate five miles off the coast of Massachusetts, has long been a summer playground for moneyed Northeasterners attracted by its 350-year-old Colonial history, 124 miles of spectacular beaches and coastline, varied and often eccentric architecture and the accepting disposition of the legendary taciturn islanders.

In recent years the island’s visibility has increased dramatically due to highly publicized visits by President Clinton and Princess Diana and the presence of such celebrities as Walter Cronkite, Billy Joel, Mike Wallace, Carly Simon, Alan Dershowitz and James Taylor.

The consequence of this fame, combined with improved transportation to the island, has been a deluge of visitors. Critical mass is reached in July and August, when the residential population explodes to 130,000 (not including tens of thousands of day-trippers), 10 times what it is year-round. On an island this small it can seem as if there’s nowhere to run, nowhere to hide.

Faced with gridlock on stone-wall-lined country roads and 45-minute waits at West Tisbury’s farmers market for a pot of plum jelly, the common refrain among locals this time of year is, “Stay calm--September’s comin’!”


Vineyard cognoscenti know that fall is the best time on the island. The crowds thin and the water is at its warmest (thanks to the Gulf Stream). Days can be spent sunbathing on the beach, but nights are cool enough to warrant a sweater. Calls for dinner reservations can be made without eliciting snorts of derision at the other end of the line. Perhaps most significantly, you can actually find a room at one of the island’s inns.

The Vineyard has a long history of accommodating visitors. At the turn of the century it was a thriving commercial fishing and shipping center (Vineyard Sound was the world’s second-busiest waterway). Starting in the 1920s, vacationers seeking a respite from city living came for the island’s deserted beaches. With such a tradition of inn keeping, it is not surprising that today there are inns all over the island.

After taking a summer home with a private beach the past few years, I have become well acquainted with many of them. They provide a welcome means of sidetracking friends, acquaintances and relatives who miraculously rediscover my telephone number at just about the time an August heat-wave is predicted in Boston or New York. A man only has so much couch space, after all.

The following is a selection of the island’s finest, selected for its geographical diversity and diverse character.


The 25-room Charlotte Inn is nestled among enormous linden and chestnut trees in Edgartown, the county seat since 1642 and the most genteel of the island’s towns, physically and attitudinally.

In contrast to the casual dress code observed elsewhere, in Edgartown you might spot a lady in a frock and bonnet or a fellow wearing a coast and tie (as a yachting center, this usually means a crested blue blazer and yacht club tie matched with lime-green pants, scuffed deck shoes and no socks). If you know Edgartown, you don’t think twice if you overhear a lock-jawed, pearl-bedecked matron calling her 70-year-old consort “Binky.”

Stately white Greek Revival houses built by wealthy whaling captains dominate the town’s three-story “skyline.” On South Water Street, in the shade of the huge pagoda tree brought from China in the early 1800s, stands the former home of Capt. Valentine Pease, master of the ship on which “Moby Dick” author, Herman Melville, made his only whaling trip. When the whaling industry faced ruin after the Civil War, many of these homes were sold and became inns.

The Charlotte Inn is the iconoclastic vision of owner and innkeeper Gery Conover, who claims he really belongs in the Edwardian era. Enter the hushed lobby adorned with 19th-Century oil paintings, approach the imposing mahogany front desk to sign in the ledger and you feel like you’ve stepped back in time.

The oldest of the inn’s three main buildings, the Garden House, dates to 1705. Each of the buildings has been painstakingly restored. Conover has spent decades accumulating antiques and artwork in Europe and the United States to make this an accurate incarnation of the Edwardian period. Most pieces look as if they belong in a museum, but are actually functional--hat stands, brass gas lamps (converted to electricity), roll-top desks and standing clocks. Conover himself cruises around Edgartown’s narrow streets in vintage cars. Thumbing its nose at convention, the inn provides TVs in only a few of its rooms;there are no VCRs, piped music, Jacuzzis and the like. All the phones are antique rotary.

Sitting on the Summer House porch on a warm fall day, the only sounds you hear may be the squeak of a rocking chair, the clink of cubes in your ice tea, or the rustling of a newspaper. Cool September and October evenings can be spent by a fire in the company of a long-neglected book. Each of the rooms has antique chests, brass lamps, goose-down pillows and comforters, vases of fresh-cut flowers and hand-made European draperies. The Carriage House Suite is perhaps the most elegant of the inn’s accommodations, with its windows overlooking Edgartown Harbor.

The inn’s restaurant, L’Etoile, is one of the island’s finest. Whether in the conservatory-style dining room, or outside on the patio surrounded by wisteria-covered wooden lattice, there is scarcely a more elegant place to enjoy dinner. Chef Michael Brisson combines classic French cooking techniques and fresh native ingredients--pheasant, quail, lobster and swordfish--with highly sophisticated results ( prix fixe $58).



The Oak House, in a 1872 Victorian mansion, stands directly across from the public beach at Oak Bluffs, a raucous jumble of Victorian pastel-colored gingerbread houses seven miles northwest on the coast road from understated Edgartown. Oak Bluffs’ architectural leave of senses was inspired by its early 19th-Century origins as a Methodist revivalist center. By the 1850s, 12,000 of the faithful camped here to attend all-day Gospel meetings.

Eventually, attendees began building permanent accommodations in the form of quirky wood cottages painted as tributes to the gaily colored revival tents. (Oak Bluff’s original name was “Cottage City.”) The homes became all the more fantastic as families entered into good-natured rivalries to outdo one another. The result has been described as “ginger-tonk.”

Ironically, given the town’s religious origins, O.B. is the Vineyard’s party town. Circuit Avenue is the island’s Bourbon Street, teeming with life until the wee hours.

Oak Bluffs was also this country’s first middle-class African-American resort. In the 1920s it was a summer haven for black musicians, writers and artists escaping Harlem. This tradition continues and, during the dog days of summer, blacks and whites mix harmoniously on Oak Bluffs’ public beach (where the movie, “The Inkwell,” was set), fishing docks, golf courses, bars and restaurants and gallery openings. Among the African-American luminaries associated with the island are Spike Lee, Oprah Winfrey and Washington lawyer and lobbyist Vernon Jordan.

The Oak House was built as the summer home for former Massachusetts Gov. William Claflin by renowned Boston architect-to-the-rich-and-famous Samuel Freeman Pratt. The governor adorned his home with handsome oak paneling and ceilings, marble sinks and exquisite leaded glass windows.

It became an inn in the 1970s. The present innkeepers--the Convery family, who are seventh-generation islanders--have meticulously maintained the Victorian ambience. Each of the 10 rooms is decorated with 19th-Century antiques. Balconies and porches take full advantage of the spectacular sunsets that dominate Vineyard Sound. The grand piano in the parlor, the rockers on the spacious porch, the high tea served by Cordon Bleu graduate Betsi Convery-Luce (make sure to elevate your pinkie when sipping), all recall a slower, more civilized era.


The Thorncraft Inn is located in a secluded part of Vineyard Haven, the island’s commercial hub. More so than any other town, Vineyard Haven functions even during winter. Shops, restaurants, hardware stores, cafes and delis bustle year-round. It’s a charming New England town of whitewashed clapboard buildings with a rich Colonial and Revolutionary history. A plaque on Main Street commemorates the site where three teen-age girls blew up the town’s liberty pole to keep it from being used as a spar by a British warship.


Holmes Hole, as the harbor is known, was once one of the busiest in New England (almost 14,000 ships anchored here in 1845). In its shelter, a ship and its crew could wait out bad weather or take on a pilot to help negotiate the rip currents and shoals that were the special perils of these waters.

When Congregationalists outgrew their tiny church in 1844, they built a Neoclassic building on Spring Street that eventually became the town hall. Known today as Association Hall, this municipal building is one of the island’s handsomest legacies of the whaling days.

A world away from downtown’s bustling boutiques and curio shops, the Thorncroft Inn’s 13 rooms are ensconced in two restored turn-of-the-century homes with four-poster canopy beds dating from the late 18th and early 19th centuries.

Owned and operated by Lynn and Karl Buder, the Thorncroft is the Vineyard’s only holder of the Mobil Travel Guide’s four-star award and the American Automobile Assn.'s four-diamond award. The inn mixes traditional amenities with modern accouterments: Most rooms have working fireplaces, as well as color TVs, air-conditioning and telephones. Some rooms have two-person Jacuzzis, or 300-gallon hot tubs.

The Buders have made their inn one of the island’s most romantic. In addition to the full country breakfast served in the dining room, a complimentary continental breakfast may be served in bed--ideal for the honeymooners and anniversary couples who make up the majority of the inn’s clientele. No lunch or dinner is served at the Thorncroft, though there is an afternoon tea with pastries in the English-style garden.


In its first season, the Inn at Blueberry Hill is one of the most ambitious projects undertaken in recent years on the Vineyard. Owners Bob and Carolyn Burgess have converted an 18th-Century farmhouse into an inn situated on 56 acres of land abutting a conservation zone in Chilmark, a picturesque community of rolling hills, spectacular beaches and stone-walled country roads.

Chilmark consists of a post office, library, community center, church schoolhouse and the general store, all clustered in clapboard splendor at Beetlebung Crossing. Chilmark is the island community most popular among celebrities. I have at one time or another spotted John Updike bicycling, James Taylor skating, Carly Simon collecting water from the spring and attorney and law professor Alan Dershowitz talking on his cellular phone naked while standing ankle deep in the ocean at Lucy Vincent Beach.

The inn offers the kind of modern amenities associated with a first-class hotel. The decor is simple, open and airy. In the guest rooms, pine and whitewashed wood and bleached cotton fabrics complement the craftsmanship of local artisans. There is an outdoor pool, a workout center with state-of-the-art Cybex equipment and spa services, such as mud facials. A fitness trainer will help you set and meet personal fitness goals. Other diversions include croquet, volleyball, boules, horseshoes and hiking in the thousands of acres of adjacent conservation land or using one of the inn’s bikes to investigate surrounding trails.

The restaurant prides itself on using only the finest ingredients. In the morning, the smell of baking croissants and brewing coffee leads you to the dining room, where awaits a selection of fresh fruits and juices, cereals, warm baked goods, homemade preserves and a gourmet tea selection. The kitchen will provide a picnic basket for lunch on the beach or a grilled vegetable sandwich on the inn’s porch.

The dinner menu, provided each morning to inn guests, gives pride of place to the freshest local offerings--herbs from the inn’s garden, organic produce and seafood from surrounding waters. The cuisine is bold, innovative and excellent.


On the westernmost part of the island, the Outermost Inn is perched atop the famous multicolored clay cliffs of Gay Head. The least populated of the island communities (there are only 300 year-round, 1,500 during summer), Gay Head is also the most laid-back. Here you feel it would be totally appropriate to quit your job, wear the same pair of shorts every day, have a love child and drive a Volkswagen bus.

Many year-round residents of Gay Head are descendants of the Wampanoag, who showed Colonial settlers how to hunt whales, plant corn and where to find clay for their early brickyards.

In fall, the air here is extra crisp. Open fields and meadows give way majestically to the Atlantic’s blue waters. In contrast to the grandiosity of many homes in Edgartown and Vineyard Haven, and the preciousness of Oak Bluffs’ architecture the homes here are deliberately understated. Even the late Jackie Kennedy Onassis’ sprawling estate is characterized by weathered shingles that blend into the scenery.

Built by Jeannie and Hugh Taylor (brother of James and Livingston), the inn is one of Martha’s Vineyard’s most exclusive. It is here that President Clinton dined with Jackie Kennedy Onassis, Vernon Jordan and Kathleen Graham when he first visited the island. With just seven rooms that are booked virtually solid through the summer, fall is one of the few opportunities to get accommodations.

Dinner at the Outermost Inn makes the most of sunset. There are two seatings--one at 6 so diners can enjoy the sunset toward the end of the meal and one at 8 so sunset can be enjoyed beforehand on the deck.

The Outermost Inn’s restaurant has one of the island’s most romantic settings. As the sun plunges into the ocean behind the Elizabeth Islands, sometimes a deer will appear silhouetted against the backdrop of pinks and oranges.

Although the inn’s prices are among the highest on the island, perhaps you can justify the expense by saving on the cost of a new swimsuit--on Gay Head public beach clothing is optional. The beach itself, which is within walking distance, is spectacular. When the sun hits the cliffs above, it lights them up in luminous layers of orange, green, white and gray.

Like Gay Head itself, the inn’s atmosphere is kicked-back. After dinner it is not unusual to repair to the outdoor bar to find Hugh Taylor singing and playing his guitar over a nightcap (a fine artist in his own right “Hughie” sounds remarkably like his brothers).



Inn Thing on Martha’s Vineyard

Getting there: Continental and USAir offer service from LAX, with most flights connecting through New York; fares start at $528 round trip. From Boston, Cape Air flies to the island, from $118 round trip.

Where to stay: In Edgartown: The Charlotte Inn, (27 S. Summer St., Edgartown, MA 02539; telephone 508-627-4151). Fall room rates (effective Oct. 16) $165-$395, suites $395-$550.

Shiretown Inn, 21 N. Water St., Edgartown, MA 02539; tel. 508-627-3353). Thirty-four rooms in four 18th-Century buildings. Fall room rates (effective Sept. 4) $89-$209.

In Oak Bluffs: The Oak House (Seaview Avenue, Oak Bluffs, MA 02557; tel. 508-693-4187). Fall room rates (effective Sept. 6) $105-$180.

The Oak Bluffs Inn (Circuit Avenue, Oak Bluffs, MA 02557; tel. 508-693-7171). Spectacular, pastel-pink “ginger-tonk” building (pictured on the section’s cover). Fall room rates (effective Sept. 4) $100-$120.

Vineyard Haven: Thorncroft Inn (278 Main St., Vineyard Haven, MA 02568; tel. 508-693-3333). Fall room rates (effective Sept. 4) $159-$309.

In Chilmark: The Inn at Blueberry Hill (North Road, Chilmark, MA 02535; tel. 508-645-3322). Fall room rates (effective Sept. 6) $158-$315. Three- and four-room cottages cost $435-$672.

The Beach Plum Inn (North Road, Menemsha, MA 02552; tel. 508-645-9454). Eleven-room inn with spectacular view of Menemsha Harbor. Fall room rates (effective Sept. 20) $110-$175.

In Gay Head: Outermost Inn (Lighthouse Road, Gay Head, MA 02535; tel. 508-645-3511). Fall room rates (effective Sept. 17) $150-$175.

For more information: Martha’s Vineyard Chamber of Commerce, P.O. 1698, Vineyard Haven, MA 02568; tel. (508) 693-0085.