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Oakdale is a scion of America's gilded age of a century ago, where powerful men of incredible wealth built South Shore gold coast mansions and dwelt in manorial splendor. Oakdale Originated from a tavern owned by Eliphalet (Liff) Snedecor in what is now Connetquot River State Park. Soon after its founding in 1820, Snedecor's Tavern began drawing New York bluebloods and business barons who wined and dined in remote joy when they weren't fishing and hunting nearby. 100%Liff's food is as good as his creek, a magazine writer declared in 1839, referring to the Connetquot River, 100%and the two are only second to his mint juleps and champagne punch; whoever gainsays either fact deserves hanging without benefit of clergy. In 1866, as the railroad reached the area, Liff's wealthy patrons formed the Southside Sportsmen's Club, and soon the race was on to see who could create the most superb spread in the thick forests adjoining Great South Bay.

The most prominent were William K. Vanderbilt, grandson of railroad magnate Cornelius Vanderbilt; Frederick G. Bourne, president of the Singer Sewing Machine Co., and Christopher Robert II, an eccentric heir to a sugar fortune. Meanwhile, William Bayard Cutting, a lawyer, financier and railroad man, built his estate next door in Great River, which had once been west Oakdale.

Oakdale was part of the royal land grant given to William Nicoll, who founded Islip Town in 1697. Local historian Charles P. Dickerson, writing in 1975, said Oakdale's name apparently came from a Nicoll descendant in the mid-1800s. The community has other claims to historical distinction: St. John's Episcopal Church, built in 1765, is the third oldest church on Long Island. In 1912, Jacob Ockers of Oakdale organized the Bluepoint Oyster Co., which became the largest oyster producer and shipper in the country.

But the mansions dominated Oakdale's past. In 1882, Vanderbilt built the most noted one, Idle Hour, his 900-acre (3.6 km2) estate on the Connetquot River. The lavish, wooden 110-room home was destroyed by fire April 15, 1899, while his son, Willie K. II, was honeymooning there. Willie and his new wife escaped. It was promptly rebuilt of red brick and gray stone, with exquisite furnishings, for a princely $3 million. The building at the time was considered among the finest homes in America. Probably the social event there was the 1895 wedding reception of Vanderbilt's daughter, Consuela, to the duke of Marlborough.

Between St. John's University and the West Sayville Country Club is an approximately 250-cottage private summer colony called West Oak Recreation Club (or W.O.R.C.). Although people believe it to be a summer camp or religious community, it is a 75-year-old exclusive, members-only colony. It should be noted that the word LILCO was scratched into the W.O.R.C. pay phone located adjacent to the "big house" in the days before the utility changed its name to LIPA, but after the period when people had to "do their business", either sitting or standing, at the communal toilets located at what was known as the big house.

Oakdale was founded around two Native American trade routes, where currently lay Sunrise Highway and Montauk Highway.

 

 



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