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Located on the Connetquot River at a point that it empties into the Great South Bay, the hamlet of Oakdale was once a playground for the rich and famous. Today, residents enjoy sailing and beaches and is recognized as one of the most beautiful areas of central Suffolk County.
Local modern history of the area began in 1697, when the land upon which the Hamlet of Oakdale was developed, was granted to William Nicoll.
In 1868, the Southside Railroad arrived in the region resulting in the influx of several millionaire families of note.
The Connetquot River State Park, a conservation area dedicated in 1967 was part of the 3,575- acre Southside Sportsmen's Club upon which the former land barons of the area hunted game.
One of the wealthy 19th century residents was William K. Vanderbilt. He built "Idle Hour", a 900-acre estate on the bands of the Connetquot River. Following Vanderbilt's death in 1927, the property was sold to independent land developers. Many of the original buildings have been placed on the National Register of Historical Places. In 1927, the 16-acre farm, a part of Idle Hour, was developed into an artists colony. Today, the "Artist Colony" is a thriving residential neighborhood that itself has attracted newcomers to the Hamlet of Oakdale.
Oakdale is served by the Connetquot Central School District, which also includes Bohemia and Ronkonkoma.
Oakdale is full of winding roads, creeks, and small bridges. The homes located in Oakdale vary from quaint mini-mansions and many blessed with magnificent views of The Great South Bay.
Easy access to the water and mannas in Oakdale provide boat-lovers with a small piece of paradise, while remaining close to home.