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. ``Liff's food is as good as his creek,`` a magazine writer declared in 1839, referring to the Connetquot River, ``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-19th century. 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 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 most important social event held there was the 1895 wedding reception of Vanderbilt's daughter, Consuelo, to the duke of Marlborough. After Vanderbilt's death in 1920, the mansion went through several phases and visitors, including a brief stay during Prohibition by gangster Dutch Schultz. Around that time, cow stalls, pig pens and corn cribs on the farm portion of Idle Hour were converted into a short-lived bohemian artists' colony that included figures such as George Elmer Browne and Roman Bonet-Sintas. Now the estate is the home of Dowling College, a fast-growing commuter school.
By 1888, Robert built a spectacular castle just east of Idle Hour called Pepperidge Hall, magnificently furnished in the French style for his young wife. But the pair didn't get along. On January 2, 1898, she told police she found Robert shot to death in his Manhattan apartment. It was ruled suicide and she moved to Paris. The mansion fell into disrepair and was razed in 1940.
In 1897, Bourne, who began with but later owned several thousand acres reaching to West Sayville, completed his mansion, Indian Neck Hall, on the east side of Oakdale. Bourne was active locally, as commodore of the Sayville Yacht Club, and was generous to the local fire department. The eastern part of his estate now comprises the West Sayville County Golf Course and the Suffolk County Marine Museum, while much of the middle portion is covered with homes. Bourne died in 1920. Six years later the mansion, on the western end, became the site of La Salle Military Academy, operated by the Christian Brothers, a Catholic order. In 1993, the brothers converted the academy into a kindergarten-through-high-school ``global learning community.`` In 2001, La Salle was closed and it was bought by St. John's University, New York.
Oakdale was founded around two Native American trade routes, where Sunrise Highway and Montauk Highway currently lie.