Founded in the mid-1650s, Freeport was originally a hamlet of farmers and baymen and was famous for its oysters. In the late 1880s, developers John J. Randall and his partner, William G. Miller, increased their real estate acreage by filling the lowlands from canals, such as Woodcleft and Randall's Bay. Hotels sprung up, and Freeport became a popular destination, drawing the rich and famous to the area's beautiful beaches and seaside activities. Entertainers found Freeport a perfect place to relax, so in the early 20th century they formed the Long Island Good Hearted Thespian Society (LIGHTS) Club and erected a world-famous clubhouse. Along with a rich entertainment history, boating and fishing (both sport and commercial) abound here. The Nautical Mile is a working port with docks for commercial fishing boats, boat dealers, boutiques, and fabulous restaurants.

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