Tuxedo Park is now 125 years old, the resort's numerical age having finally caught up to its carefully antiqued design.

When construction began in late 1885, the 5,000-acre plot, about 40 miles northwest of New York City, was home to a shuttered ironworks and not much else. By the following spring, the frenzied labors of nearly 2,000 Italian and Slovak workmen had produced 18 miles of lamplit macadam road, a 100-foot swimming pool, stables, a fish hatchery, a sewage treatment plant, a telephone network, 15 cottages, and a four-story clubhouse, all of it ringed by an eight-foot-high barbed-wire fence, accessible only through a single gate that Bruce Price, the project's architect, said looked "like a frontispiece to an English novel." Per Price's instructions, the cottages' shingles were stained to appear aged; moss on the masonry was encouraged.

Lunch at 19th-century financial titan George Fisher Baker's former carriage house, now a family dwelling. PHOTOGRAPHY BY JONATHAN BECKER

Conceiving, bankrolling, and micromanaging this ambitious project was Pierre Lorillard IV, of the Lorillard Tobacco Company — the oldest publicly traded company on the New York Stock Exchange and progenitor of such marvels as rolling tobacco and the prerolled cigarette. (The word millionaire appeared in American print for the first time describing Lorillard's grandfather, Pierre II.) Lorillard was an adrenaline junkie avant la lettre: competitive racehorse breeder, yachtsman, gambler, and even amateur archaeologist. After unloading his Newport home, the Breakers, onto Cornelius Vanderbilt, Lorillard turned his mercurial attentions to an inherited tract in New York's Ramapo Highlands, envisioning a rustic hunting retreat for a few well-born friends. Of his client, Price said, "He talked rapidly and thought twice as fast as he talked, and wished his order carried out at a speed that equaled the sum of both." Another observed that Lorillard "ordered houses in the same way that other people might order boots."

After unloading his Newport home, the Breakers, onto Cornelius Vanderbilt, Pierre Lorillard IV turned his mercurial attentions to an inherited tract in New York's Ramapo Highlands, envisioning a rustic hunting retreat for a few well-born friends

On opening day — May 31, 1886 — hundreds of prospective Tuxedo Club members arrived by chartered train, and in short order John Jacob Astor, William Waldorf, Cornelius Vanderbilt, and William Whitney were all paying dues. (Membership back then was $100 a year.) The Tuxedo Park Association, 99 percent of which was owned by Lorillard, fronted the cost of municipal functions (for which it was duly reimbursed by the Property Owners Association) and managed all property sales.

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In good years the TPA paid a healthy dividend; in bad years its board of governors covered the Tuxedo Club's deficit out of pocket, settling the difference (legend has it) among themselves over a gentlemanly hand of poker. The name Tuxedo, as a committee chaired by William Waldorf Astor determined in 1888, was an anglicization of the Algonquin ptauk seet tough, or "place of the bear" — an inelegant, if accurate, designation, residents say.

Henry Poole told Tuxedo resident James Brown Potter the Prince of Wales had lately taken to wearing a short satin-lined jacket in the evenings and advised him to order one of his own.

Regarding the origins of the eponymous dinner jacket, theories abound. The most widely accepted explanation goes like this: Preparing for a weekend with the Prince of Wales (later King Edward VII) in 1886, Tuxedo resident James Brown Potter consulted Savile Row's Henry Poole & Co. to ensure that he would be properly outfitted in such company. Henry Poole told Potter the prince had lately taken to wearing a short satin-lined jacket in the evenings and advised him to order one of his own. Upon Potter's return, Lorillard and a friend had their own copies made, and after a few promenades at Delmonico's, tails were out forever.

A short list of Tuxedo's notable residents would have to include Henry William Poor, co-founder of Standard & Poor's, the rating agency that recently downgraded America's creditworthiness; Augustus D. Juilliard, whose foundation became the Juilliard School, famed for its performing arts program; Emily Post, Price's daughter, who became the immortal authority on the subject of her book Etiquette, continuously in print since 1922; original "bankster" Charles E. Mitchell, president of National City Bank (now Citi); Alfred Lee Loomis, financier and amateur physicist whose covert basement laboratory, visited by celebrated scientists, was responsible for subsequent breakthroughs in radar technology; Dorothy Draper, who went on to decorate the Drake and Carlyle hotels; both New York governor Thomas E. Dewey and the president he famously failed to unseat (notwithstanding the greatly exaggerated reports to the contrary), Harry S. Truman; pop songwriter Jimmy Webb, best known for the seven-minute "MacArthur Park"; and, most recently, Whoopi Goldberg.

The Great Crash of 1929 decimated many Tuxedo fortunes, and the costs of staffing and maintaining second, third, or fourth residences became a burden, or worse. An insurance investigation revealed that prominent stockbroker Colonel Frank Browne Keech had paid his chauffeur to torch his Tudor Revival estate; Keech died a few weeks before his trial, jumping onto the Lexington Avenue subway tracks as a train barrelled into the station.

Over the following decades some properties fell into disrepair; others were carved up into multiple dwellings. Several of the ones pictured in these pages once housed gardeners, chauffeurs — even horses. They have found new glory as comfortable full-time residences, or weekend retreats, for the latest generation of villagers, all 623 of them. (Metro-North Railroad's Tuxedo station deposits passengers virtually at the entrance to Tuxedo Park, maintaining a vital link to New York City.) Meanwhile, many of the original manors, once so vastly patrician in scale, lie in ruins — a scene more timeworn and romantic than the founders could ever have thought possible.

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