Welcome to Rhode Island's oldest resort town, where it's now possible to picnic on the lawns of million-dollar mansions and mingle with heiresses at velvet-rope nightclubs.
Patrick McMullan

The ritual of brunch at Bailey's Beach, a private club where the oldest Newport families still come to be rich and thin together, is an ancestral and vaguely incestuous mosh pit. A turn-of-the-century institution that was rebuilt after the hurricane of 1938 and frequented by a succession of nicely aged bloodlines, the rambling assortment of simple cabanas and no-fuss buildings is still run by the Spouting Rock Beach Association (it takes its name from the tidal spume that gushes up through a nearby cliff).

Next to the haves of life who typify Bailey's are the denizens of tiny "Rejects Beach," an eternal joke used by members to describe the unanointed who lurk and swim around the fringes of the club, which is nestled in a rock-adorned cove. Save for the cutting wire of class, no fence separates the public from one of America's most exclusive and secretive clubs, a very private enclave of WASP aristocracy. All beaches are open to ordinary mortals in Newport, though the aesthetic hierarchy is as invincible and mysterious as the pecking order among stray dogs: Bailey's has the best-looking, thinnest, best-mannered crowd; Rejects is close behind; and the larger beaches down the road, such as Gooseberry, are dotted with potbellies, beer coolers, and average Joes.

In Newport, as in many places across America, country clubs are semiotic semaphore, guideposts to a certain kind of existence on the hamster wheel of status. Bailey's Beach is particularly intricate. A sign at the clay courts reads TENNIS WHITES ONLY, but there's also that primal summer aroma of cheeseburgers and hot dogs, as well as a saucy cartoon in the lobby, of dogs standing at a urinal. Weekends are a gentle hum of giggling children, clinking glasses, the prancing of golden youth, clambakes, and where-have-all-the-good-times-gone hangover chatter.

Throughout a cozy meal, I'm careful not to openly take notes, my hosts having warned me that journalists—especially visiting social reporters like myself, from nouveau Miami—are beyond the pale in the Bailey's pantheon. But after lunch, one of the glossier kids introduces himself and promptly dismisses the circumstance of his last name on the Bailey's legacy list. All that old family nonsense is so, well, old to bright young things leaping into the new age: "You're from Miami, right?" he says. "I DJ all over the place. I'm going down to South Beach next week to spin at this club. You should write about me, maybe something like, 'The little rich kid who could.'"

And so it goes in Newport, the little rich town that could, firing on all cylinders on the kind of flawless day that inspired Newport devotee Henry James's unequivocal utterance to Edith Wharton: "Summer afternoon; to me those have always been the two most beautiful words in the English language." Much of the beauty remains the same—countless classic wooden sailboats still tack across Narragansett Bay, though surfers are also now part of the equation—and downtown contains America's largest collection of 17th- and 18th-century architecture. As in Wharton's day, the clash between old and new money is always bubbling up through the shiny surface of life in Newport—a battle sharpened by a real estate boom and flare-ups of Hamptons-style flash. The cultural tone of the town is still poised between the bold sophistication of New York and the quieter cultivation of Boston, a subtlety perhaps lost on the endless day-tripping hordes swarming over the T-shirt-and-taffy-shop-filled harbor area. For regular Rhode Island folk, the Providence crowd and such, Newport is just a day at the beach and a stamping ground for nightlife. The weirdest little resort in America, Newport is a place with muscle—like Key West, Maine, and Plymouth Rock going out on a bender and spawning a hardy mutant. It's everything at once to every kind of visitor (sometimes too much in summer), but somehow, it all works.

Newport's claim to intellectual and moral rectitude has a tenuousness that goes back to 1639. The early settlers included not onlysummering plantation owners but also a motley crew of refugees from rampant Puritanism—slave-traders, pirates, smugglers, rum distillers, whale-blubber tycoons, and general vulgarians. Such cultural luminaries as Henry Wadsworth Longfellow, Henry James, and his brother, William, came later. For a short time before the American Revolution, Newport rivaled New York and Boston as a seaport. Things slacked off throughout the Depression; it then entered a raucous whorehouse-and-tattoo parlor period as a Navy tomcat town. After the Second World War, the Preservation Society of Newport County helped resuscitate the town's romantic past, especially along Bellevue, the avenue of dreams where the robber barons built their grand "summer cottages." The houses cost millions in 19th-century dollars, with the great architects of the day—Stanford White, Richard Morris Hunt—moving in for a killing. Each property has a morsel or two of beauty, such as the whimsical 1914 Chinese Tea House on the grounds of Alva Vanderbilt Belmont's baronial Marble House, or Mrs. Hermann Oelrichs's 1902 Rosecliff, which found its way into the Robert Redford film adaptation of The Great Gatsby. But the cumulative effect is Beverly Hills with a chill, depressing in a Day of the Locust way. On the hour, every hour, the bus tour crowd shuffles through the vast rooms and gapes at all the gilt like atavistic pilgrims, genuflecting before their dead betters.

In the end, many American creations have the potential to turn into Disney World, though Newport's history is put to good use day and night. Cliff Walk, a public path that winds along the oceanfront behind all the epic assertions of commerce, is a unique experience in this era of gated communities: on pretty days, local families have picnics on the lawns of unused mansions. And the best social sightseeing value in the country might be the summer rite of the $40-a-ticket garden party at the Redwood Library & Athenaeum, a kind of cultural clubhouse brimming with civility and Gilbert Stuart portraits, in continuous and well-bred operation since 1747. Outside, amid the gentle lawns and stylized topiary, a roiling ocean of Ascotesque sun hats, straw boaters, and colorful blazers—apparently inspired by the sherbet counter at Baskin-Robbins—make air-kiss conversation.

Saturday night at the candy store, where Warhol dined in celebrity state and the Farrelly brothers once worked as bartenders, is a New England version of New York in its 1980's a-go-go heyday.The circa-1780 building is officially named the Clarke Cooke House: natives call it the Candy Store, in memory of the days when the first floor was a combination bar and candy shop. Now it's a 25-year-old institution of the American caste system, a swarming anthill that contains the entire social hierarchy of Newport: the basement level is the Boom Boom Room, a sloppy dance club, and the first floor is for non-connected tourist-trade chumps. Most of the second floor, blocked off with velvet ropes, is for locals and yacht crews. On the awning-covered roof, the Sky Bar, protected by yet another set of ropes, a certain strain of society—from decadent trustafarians to patrician members of the ruling class—shows up every single summer weekend for dinner, dancing, and the indigenous art form of gossip.

Around midnight, the staff pushes back the tables at the Sky Bar, and the dancing commences with the eerily prophetic "Play That Funky Music White Boy." The arrival of Dennis Conner, who's won the holy grail of the America's Cup, creates an instant buzz: Newport is the national capital of yacht racing, and the town has never been the same since Conner lost to Australia off Newport in 1983. Conner is traveling tonight with his benefactor, Bill Koch—a great big piñata—and a man introduced as Rod Stewart's guitarist. The well-born Harper's editor Lewis Lapham turns up on the dance floor among the frug and fox-trot set, a glistening assortment of brand names that includes Andrew Roosevelt and the stunning Hilary Dick, a du Pont by birth. "As kids, we couldn't wait to sneak in here," Dick says. At closing time, the DJ plays the last-call standard, Kate Smith's version of "God Bless America."

Newport's nightlife is never boring, unlike that of some choking-with-chowder-and-anomie New England summer towns. In the emerging Broadway district—Newport's version of the East Village—there's Pop, a bright orange-and-yellow spot with candles and a fireplace (the sort of place that serves mashed potatoes and tenderloin tips in martini glasses). El Diablo's, a tiny Asian-Mexican fusion café, has a sound track that jumps from Hank Williams to Iggy Pop. Down the street is Salvation Café, a similarly jolly fifties-style joint. On the fringes of Broadway, Billy Goode's Tavern—a former speakeasy—brims with a cross section of workingman society: a huge former cop is singing a delicate show tune for some Portuguese fishermen. Originally a male-only establishment—the policy didn't change until legal action was taken in 1977—Goode's used to open at 6 a.m. One regular proudly notes: "This has always been an alcoholics' bar." Around the corner, another low haunt is also embracing the life-is-a-cabaret dialectic. A group of lads gone wild have erupted into an inchoate roar, shirtless and shoving one another as if they were Mongol warriors. At all levels of Newport society, a problem drinker is someone who can't keep up—if only the Puritans could come back and frighten off the nightly spectacle of stumbling frat boys and local drunks.

At this hour, the waterfront is looking even more squalid than usual, so my expedition team and I hop into a borrowed Jaguar for a mansion tour. We tool past Lands End, the former residence of Edith Wharton—and stop in front of Clarendon Court, the former residence of Sunny and Claus von Bülow. Out of nowhere, a well-dressed man runs pell-mell down an empty street off Bellevue, up to no good but politely pausing at the stop sign, a bad David Lynch movie come to life.

Unfortunately, the sober Starbucks has set up camp downtown (along with such monstrosities of the 1970's and 80's as the seven-story Marriott on America's Cup Avenue, Brick Marketplace, and the enormous Hyatt Regency on nearby Goat Island). On the other hand, fishing boats still come to the very real docks behind the Aquidneck Lobster Co. on Bowen's Wharf; Clarke Street boasts an unbroken ribbon of 18th-century bed-and-breakfasts; and the Jane Pickens Theater, named after a local society girl radio star, is a conceit of pure fifties movie house charm. Here and there, the clapboard walls of old buildings have bowed out over time like overripe tomatoes, adding an improbable beauty their builders could never have envisioned.

Now downtown works as a model of New Urbanism, obeying all the pedestrian-friendly, mixed-use laws of that development movement without the unsettling perfection of its brand spanking new neighborhoods. A short walk from the harbor is the Point, a time-warp section of town with absolutely no tourist-driven establishments. Many of the simple houses and perfect little gardens are named after their builders—the Elliott Boss House, 1820; Hunter House, 1748—and feature carved pineapples, a seaport symbol of hospitality. The more lavish waterfront properties on Washington Street yield to the slightly funkier ones on Second Street, and on the weathered front porch of an old house converted into apartments, a group of neighbors have gathered for a barbecue. Theresa Wosencroft is enjoying the soft dusk as the host, Artie Jenkins, laughs and hands me a beer: "You're in the ghettoized section of Newport," he tells me. "We don't have yards, just porches. Stay awhile and have some dinner." Earlier in the day, I spent an hour at the Bellevue Avenue house of an acquaintance from Miami and wasn't even offered a glass of water, despite the presence of a hovering butler. Newport is always good for a social lesson or two.

True fun is a democratic proposition, and just out of town on Memorial Boulevard lies a string of beaches—Easton's, or First Beach, then Second Beach—spread out like a familyland paradise, with a vintage carousel, a frozen-lemonade truck, and the Newport Exploration Center, a satellite of the New England Aquarium. Farther along is the Sachuest Point National Wildlife Refuge, the wonderful Norman Bird Sanctuary, and the less crowded Third Beach. On the other end of town, picnickers can join the hundreds of kite fliers at Brenton Point State Park, take in the Museum of Yachting at Fort Adams, or simply bask in cocktail nirvana on the vast waterfront lawn of the Castle Hill Inn & Resort, which resembles a great big wedding cake. On weekends, just down the road from the inn, the old-line stalwart Minnie Cushing Coleman, once married to photographer Peter Beard, puts out an assortment of eggs—collected from her own chickens—by the front gate of her cottage, for sale on the honor system to whomever might drive by.

But the absolute best public attraction in Newport is Rough Point, the former home of one of its wealthiest residents, Doris Duke, who died mysteriously in 1993 as a tabloid star, with butler and companion Bernard Lafferty, the U.S. Trust, and assorted lawyers fighting over her billion-dollar estate. These days Duke's Newport Restoration Foundation runs her holdings in town, including some 79 restored and rented-out Colonial houses. (Duke used to buy up stretches of city blocks like a Monopoly kingpin.)

Rough Point had been yet another Vanderbilt outpost,constructed on 10 acres in 1891, with landscaping by Frederick Law Olmsted. In 1922, Duke's father, tobacco magnate James B. Duke, bought the place, poured money into an ambitious renovation, and then promptly passed on, a phenomenon the natives call "Fix-up, croak, and Sotheby's." Doris was his only child, a 12-year-old whose ineffably sad portrait still hangs in the grand staircase. The poor little rich girl grew up to be a renowned beauty, art collector, pianist, wanderer, and animal lover. Two camels, Princess and Baby, once strolled the grounds of Rough Point.

Duke also kept estates in Beverly Hills, New Jersey, and Hawaii; Rough Point has been left exactly as it was when she died—a 1971 Architectural Digest is lovingly displayed on a table as if it were fresh from the printer—and is deranged in the best possible way. The decorative jumble includes a 1780 Joshua Reynolds portrait of the Duchess of Marlborough, a set of 1510 Flemish tapestries, needlepoint pillows that read MY DECISION IS MAYBE AND THAT'S FINAL, parquet floors imported from a French château, and a mirrored disco ball dangling over the basement pool. Duke's cotton robe and cheap rubber bathing cap still hang in the changing room. In the truly insane master bedroom, a blinding set of Charles X mother-of-pearl furniture is accented by purple curtains, yellow walls, Renoir's Portrait of a Young Girl Sewing, and Duke's 1920's trophy from a Bailey's Beach sandcastle contest.

The longtime estate manager, Phil Mello, has an interesting perspective on the gestalt of Rough Point. When asked about the more celebrated houseguests, he flips through a little black address book to refresh his memory: "Well, there was Liz Taylor, Martha Graham, and Jim Nabors. Burt Reynolds stayed here, along with that pretty ex-wife of his—that's right, Loni Anderson. And Imelda Marcos was always in the house: her maids would sit up all night long in her room while she slept."

The history of loot is everywhere in Newport and not pretty: invariably, the farther you get from the money, that fetishized ecosystem of grand houses and private clubs, the better life becomes. For a supposedly tasteful little resort, the high end of town is awash in an endless din of suffering and schadenfreude. Much of the town's pain emanates from the clubs and all the "unclubbable" newcomers who are excluded from being members. But wherever you go, someone or other can't wait to tell you something juicy about their best friend, or about the mighty doyenne of old-guard society whose son has just been indicted on polite white-collar crime charges, or the unmitigated gall and extravagance of the newest arriviste. Suddenly, none of Bellevue Avenue, the boulevard of ashes and dust, seems worth the cost, a toll taken that Mello understands all too well: "The very rich are funny people and lonely as hell. Even in Newport, there's such a thing as too much money."

Tom Austin is the features editor at Ocean Drive Magazine.

The Facts

Newport is a 30-minute drive from Providence, a 90-minute drive or train ride from Boston, and a 3 1/2-hour trip from New York City, either by car or train. July and August are high season in Newport, and on weekends, downtown can be a crowded mess. Make hotel and restaurant reservations well in advance.

Admiral Fitzroy Inn A quaint-beyond-measure 1854 bed-and-breakfast. DOUBLES FROM $165. 398 THAMES ST.; 866/848-8780 OR 401/848-8000; www.admiralfitzroy.com
Castle Hill Inn & Resort This Victorian mansion on a 40-acre peninsula has stunning views of Narragansett Bay. DOUBLES FROM $395. 590 OCEAN DR.; 888/466-1355 OR 401/849-3800; www.castlehillinn.com
BEST VALUE Francis Malbone House Designed by Peter Harrison—who also did the Touro Synagogue and Redwood Library & Athenaeum— the 1758 creation is the town's most beautiful historic inn. DOUBLES FROM $285. 392 THAMES ST.; 800/846-0392 OR 401/846-0392; www.malbone.com
Hotel Viking The Viking began life as a guesthouse for the Bellevue Avenue mansions. DOUBLES FROM $279. 1 BELLEVUE AVE.; 800/556-7126 OR 401/847-3300; www.hotelviking.com
OceanCliff Hotel Built in 1864 as a private estate, the 24-room clifftop hotel has every conceivable luxury—like oceanfront tennis courts. DOUBLES FROM $350. 65 RIDGE RD.; 401/841-8868; www.newportexperience.com
Sanford-Covell Villa Marina In the Point section of town, this waterfront inn has a wraparound porch and spectacular sunset views. DOUBLES FROM $160. 72 WASHINGTON ST.; 401/847-0206; www.sanford-covell.com
Vanderbilt Hall In 1909, the Vanderbilts gave the property to the city of Newport; it's been a hotel since 1997. DOUBLES FROM $265. 41 MARY ST.; 888/826-4255 OR 401/846-6200; www.vanderbilthall.com

Asterisk A trendy hangout with a collection of drawings related to circus sideshow acts. The Newport Bouillabaisse—rouille, croutons, and Gruyère—is a tradition. DINNER FOR TWO $75. 599 THAMES ST.; 401/841-8833
Billy Goode's Tavern 23 MARLBOROUGH ST.; 401/848-5013
Clarke Cooke House DINNER FOR TWO $125. BANNISTER'S WHARF; 401/849-2900
El Diablo's DINNER FOR TWO $60. 1 FAREWELL ST.; 401/845-6664
Flo's Clam Shack The "lobsta" rolls, renowned fried clams, and high kitsch—such as a collection of Miss Rhode Island memorabilia—make this 67-year-old Easton's Beach institution a wonder unto itself. LUNCH FOR TWO $25. 4 WAVE AVE.; 401/847-8141
Pop DINNER FOR TWO $45. 162 BROADWAY; 401/845-8456
Salvation Café 140 BROADWAY; 401/847-2620

International Tennis Hall of Fame Contained within the 1880 Newport Casino, the complex has a comprehensive museum dedicated to the sport. ADMISSION $8. 194 BELLEVUE AVE.; 800/457-1144; www.tennisfame.com
Newport Restoration Foundation The foundation runs tours of Prescott Farm, the Samuel Whitehorne House Museum, and Rough Point, Doris Duke's former estate—a much less crowded and vexing experience than the other mansion tours. ADMISSION FROM $8. 51 TOURO ST.; 401/849-7300; www.newportrestoration.org
Norman Bird Sanctuary A wildlife refuge and education center on 400 acres, with seven miles of trails. ADMISSION $4. 583 THIRD BEACH RD., MIDDLETOWN; 401/846-2577; www.normanbirdsanctuary.org
Preservation Society of Newport Some 11 historic mansions and other properties—including the Breakers, Marble House, and Rosecliff—are open for public tours. ADMISSION FROM $10. 424 BELLEVUE AVE.; 401/847-1000; www.newportmansions.org
Redwood Library & Athenaeum This calm haven away from the tourist chaos may be the most elegant building in town. 50 BELLEVUE AVE.; 401/847-0292; www.redwood1747.org

Flo's Clam Shack

El Diablo's

Clarke Cooke House


Salvation Café

Excess of a more approachable kind rules at this kitschy and acid-hued diner, which serves globally influenced dishes—that still nod to the region’s coastal heritage—like fennel-lobster bouillabaisse Marseilles.


Castle Hill Inn

Vanderbilt Grace

Sanford-Covell Villa Marina


Hotel Viking

Francis Malbone House

Admiral Fitzroy Inn